A Tale of Regret: People Share The Worst Dates of All Time

A Tale of Regret: People Share The Worst Dates of All Time

Everyone's always out there searching for love, but unfortunately, it's never as easy as it seems. If you're feeling like you ran out of luck, don't worry, you're definitely not alone. From rude dates throwing out insults left and right, to entitled ones just there for the free food, to meeting people who turn out to be NOTHING like they said they'd be, there are a lot of ways your date could take a turn for the worst. But don't just take it from us, these shocking stories about terrible dates will have you amazed by the horrible experiences these people have gone through.

1. The Cold Ride Home: A Story of Cheating and Heartbreak

My ex and I had been together almost 2 years when we went to see a movie. We stopped to eat beforehand, but I realized she hadn’t been talking much. 

“What’s wrong?” I asked. She said nothing of course, so I kinda brushed it off and tried to keep making conversation. She was still pretty quiet, but I thought, “Well, maybe watching this movie will cheer her up!”

I went to buy our tickets and drinks but she was still acting distant. I tried holding her hand in the theatre but she pulled her hand away. Then without talking (even though I was right next to her!), she pulled out her phone and typed, “We’ll talk after the show.” 

When the movie ended, I was trying to discuss some of it with her. I was pretty sad because of how the movie ended, but she made my night even worse. We get in the car and she suddenly laid it on me. “I cheated.” I completely broke down. Apparently, it had been going on for months and she told me she loved him. How classy of her to make me pay for dinner and a movie before telling me. That final ride home was super cold and awkward.

A couple of months later, she broke up with the guy she cheated on me with. She even tried getting back into my life, but I didn’t let her. She’s been in a new relationship for almost a year now, and I’m completely incapable of loving another human being again after that experience.

kelly-sikkema-E8H76nY1v6Q-unsplash-1024x683.jpgPhoto by Kelly Sikkema on Unsplash

2. A Chatroom Encounter Gone Wrong: How One Date's Desperate Act Changed My View of Online Dating

I met a girl in a chatroom way before dating/hook-up sites were a thing. We chatted for a while and decided to meet in real life for dinner. When we met, I discovered she was deaf, which wasn’t a big issue. We communicated by writing on a notepad she carried. We had a pleasant dinner and I drove her home. I declined the offer to come in and went home thinking that we made a connection. The communication was a bit of an issue though.

In the next few days, she started calling me. The phone company at the time had a service where the deaf could type to an operator who would transcribe the text and type back my side of the conversation. She started getting very sexually explicit even though we had never had any type of physical contact up to this point. This made me pretty uncomfortable, especially because the words were coming from an unknown operator at a phone company.

After that, I pretty much ghosted her. Between how quickly she jumped from a pleasant dinner to a sexually explicit third-party conversation, things were somewhat too overwhelming. She tried contacting me a few times in the next week between phone and chatroom messages, but I didn’t respond. 

A couple of days later, she was in the news for trying to murder/suicide herself and her two children. The story is that she fed her kids a bunch of medication and swallowed a bunch of pills herself. She then went to the chatroom we frequented and told others what she had done. They got the police and rescue involved to save her and her children. I’ve had some guilt over this, but honestly, we only chatted online a few times and I took her out to dinner once. Maybe if I had communicated better with her, this wouldn’t have happened, or maybe I just had nothing to do with it. I was never told why she did what she did, but I can tell you this ruined me for online dating.

absolutvision-WYd_PkCa1BY-unsplash-1024x683.jpgPhoto by AbsolutVision on Unsplash

3. Checklist Date: A Unique Experience I Couldn't Quite Get Over

A few years ago, I went on a date with a girl I met on Tinder. We agreed to meet at a restaurant and when she arrived and sat down at the table with me, she then proceeded to pull out a clipboard with a checklist. She asked me a bunch of questions. Things like, “Do you want kids? If so, how many?”, “What political party do you align yourself with the most, and why?”, “What is your major and what are the average salaries for entry-level jobs in that field?”, “If your wife made more money than you, would you be willing to sacrifice your career and be a stay-at-home dad?”

In total, there were like 30 questions. At the end, she put the clipboard back in her backpack and then continued the date like a normal person. When I asked her what that was about, she told me it was something she’d been doing to make sure someone’s goals and values were similar to hers. I finished the date, but I just couldn’t quite get over the checklist thing.

glenn-carstens-peters-RLw-UC03Gwc-unsplash-1024x681.jpgGlenn Carstens-Peters on Unsplash

4. My Unforgettable First Date with My Boyfriend - A Bird Poop Story

I had the most unforgettable first date with my boyfriend. It started off great, we were walking around, enjoying the day, until the most unexpected thing happened. Two birds, within half an hour, decided to use me as their personal toilet. One of them even managed to land in my hair! My guy was so sweet though, he immediately sat me down on a bench, gave me a tissue to clean up the mess, and helped me get the bird droppings out of my hair. Despite the shock and embarrassment of the situation, we ended up having an amazing date. We've been together for two years now and I still can't believe what happened that day!



5. My Horrible Date and the Nasty Mead He Gave Me

This was in college, I was so excited to meet my online date. But when he arrived, he was 6 inches shorter than he said he was! We went into the restaurant, where he said he had already eaten, so I had to quickly scarf down my sandwich while he watched me. To make matters worse, he followed me back to my dorm and wouldn't leave until I made up a pressing appointment in a building he didn't have access to. As a parting gift, he gave me six bottles of his homebrewed mead - which my friend said was nasty stuff! What a horrible date!


6. My Worst Date Ever: A Story of Fainting and Hunting

I once went out with this guy who had been kind of pestering me for months to go out to dinner with him. I agreed because I thought maybe he would lay off a little if I just gave in and ate a meal with him. He was very good-looking and we had some mutual friends, hung out at the same bars, clubs, etc., but something about him always struck me as odd. 

So he picks me up and gives me a rose as he is opening the car door for me. Usually, I would have been flattered, but again, it kind of gave me the creeps for some reason. To top it off, on the way to the restaurant, I started feeling very queasy and lightheaded. He pulled over to a gas station and I got out to go inside and get a bottle of water. When I got out and stood up, I immediately felt as though I would pass out and fall to my knees. I was shaking and feeling like I was about to black out at any moment. I managed to get inside the store, bought some water and a power bar, and it eventually passed. So already, this is not turning out to be a great night.

We get to the restaurant, and it’s very nice. I’m feeling like I’ve recovered from the earlier fainting spell. As we’re sitting waiting for our server to come over, he starts randomly telling me how much he loves to hunt. Actually, he tells me he loves to KILL things and is very very skilled at it. Keep in mind, I’m a huge animal lover and really hate to see them hunted down. 

He just keeps going on about all of his knives and how he enjoys killing. Then he actually said that if he ever killed a human, he knows that he would be able to do it so well that no one would ever know or find the body. I was so HORRIFIED, but I tried my best to hide it. I casually told him that I needed to use the restroom and while I was inside, I called a cab. I waited a few minutes and thankfully the taxi was fast. I was able to sneak past my date, run outside to the cab, and go home. I have never done anything like that before, and I would normally never condone something so mean, but I swear I was actually concerned for my own well-being. Something in my gut told me to get out of there! I had to find new places to hang out after this, but it was worth it to never run into this guy again. That’s my worst date story.

paul-einerhand-gIp8WnFJrSU-unsplash-1024x683.jpgPhoto by Paul Einerhand on Unsplash

7. Don't Get in the Car of a Stranger You Met on POF!

Met this guy on POF and we had dinner at O'Charleys. He was driving me crazy, so I stupidly got in his car and he wanted to drive to a desolate warehouse area. On the way back to the restaurant, he pulled into an assisted living place for the elderly, claiming his friend was looking for one. He started picking and eating vegetables from their garden, which made me think he must have done this before. I researched his telephone number and found out he was recently married and had a string of domestic violence charges. I'm still here to tell the tale!

markus-spiske-4yK8iDaWnm8-unsplash-1024x683.jpgPhoto by Markus Spiske on Unsplash

8. Dating Disaster: Three Unexpected and Uncomfortable Experiences

It had been a while since I was on a date, so I decided to give it another try. Unfortunately, I was quickly reminded why I had stayed away from the dating scene for so long. On three consecutive dates, I experienced some of the most unexpected and uncomfortable moments. On my first date, an acquaintance of my ex showed up and refused to leave, asking if we were still together. On the second date, a drunken man with a cup full of rum joined us and asked if we were interested in having some fun. On the third date, a well-known local creep came crashing through the bushes, popped a squat with us, and forced us to leave. Needless to say, I was done with dating for a long time thereafter.

dev-asangbam-_sh9vkVbVgo-unsplash-683x1024.jpgPhoto by Dev Asangbam on Unsplash

9. Unwanted On A Date: A Lesson Learned

Mine was simple, but it made me feel really hurt.

I had a crush on a guy and when I finally was on a date with him, I was really happy. We were eating and we randomly remembered a mutual friend (girl) we had in common that was studying at a university nearby. He told me he thought she was really cool and I agreed. Out of nowhere, he decided to pick up his phone and call her to join us for dinner. At that moment, time stopped and he made me feel like the ugliest and most undesirable girl in the world.

m-T9THJMIIMPM-unsplash-1024x682.jpgPhoto by M. on Unsplash

10. My Horrifying Date with a Creepy Russian Revolution Enthusiast

This guy and I had a mutual friend in real life. Whenever we met through her, he would hug me so I thought, “Fine, what the hell. One date is alright, he seems fine.” But the minute we got into his car, I was talking about chilling and playing video games when he suddenly whipped out his junk. 

I tell him I’m uncomfortable because I can still see my friends walking past his car. He decided to put it away and when I told him where I lived, he said, “Too far, we should get food instead.” Sure, why not. 

Five minutes into the drive, he pulls it out again and starts talking about how he loves traveling and wants to be President one day. He starts to play Russian Revolution music even though he wasn’t Russian. Anyway, the moment we got to the drive-thru, he started flirting and joking with the girl taking his order. He then proceeds to take out his junk AGAIN while ordering! I’m in disbelief at this point.

He then drives forward and puts it away before getting to the window. He spent the rest of the night eating food and talking about how “fat” he was and how “gross” he was. I said he wasn’t because he really wasn’t fat, he was just fishing for compliments. He finally said he was going to take me home and I’m thinking I’m getting out scott-free when he sees an empty library parking lot. “We can hook up there!” he exclaimed.

He parks and I reluctantly perform an intimate act just to hurry things along. He gets off but I do not. After that, he pissed in front of me on a tree and started discussing the political standing of Syria in the Middle East. To this day I’m still not sure why I didn’t just barrel roll out the door and onto the side of the road.

christian-erfurt-sxQz2VfoFBE-unsplash-1024x768.jpgPhoto by Christian Erfurt on Unsplash


11. Don't Try Dating Your Friend: My Humorous Experience

For some reason, I decided to go on a date with a friend. I was totally willing to go half and half on the date, but he told me no and to get whatever I wanted. I ended up getting 2 shots of the lowest-tier vodka and a chicken dinner which was the cheapest item on the menu.

When he saw what I ordered, he BERATED me because apparently, I was taking advantage by getting “expensive” stuff (the vodka). I explained that the vodka I got was half-price for the hour, and it was only $3 a shot. The chicken was only about $5 for the entire meal too. I offered again to pay for half and basically got yelled at for suggesting he couldn’t afford it.

After we left the restaurant, I got a 20-minute lecture about how greedy and rude I was as a date. Blah blah blah. He still somehow expected me to go back to his place and he even tried to kiss me! Needless to say, I told him nicely we were much better as friends and that I’d pay him back for the date at the bar the next time I saw him.


12. My Worst Date Ever: A Formula One Driver Who Wouldn't Stop Talking

I stupidly went to his house. He was a Formula One driver, and I couldn't get a single word in during his monologues about F1 history, drivers, engines, and when the chassis design changes occurred. It was the worst, most boring, one-sided hellish experience in dating captivity I've ever had. I must've pet a bald spot into his cat from how horribly frustratingly awful it was.

It got to the point where I had one of my co-workers call me- at 8-something PM on a snowy night an hour away from home- and explain that he needed ME, his boss, to come in to work to handle the crises occurring in the ER because our on-call and back-up on-call folks just couldn't do it. He even went so far as to argue with me on the phone to make it sound legit. I'm so glad it worked and I left and blocked the guy and have never looked back.

jesper-giortz-behrens-yn8-sVBtys8-unsplash-1024x683.jpgPhoto by Jesper Giortz-Behrens on Unsplash

13. When People Watching Exposes Her True Colours

I’ve shared this before, but one time I was out on a first date with this girl I met online. I thought she was very attractive and we seemed to hit it off well through texts.

We’re at this bar and she suggests we play a people-watching game where we try to make up backstories for the other people here. I thought it sounded fun, especially since I played a similar game with friends on the train sometimes. Plus, it felt like a good icebreaker to get us talking.

Well, she managed to take all the fun out of the game by being RIDICULOUSLY cruel in all her assumptions for no reason at all. It felt like she was projecting issues she had onto these people. Like one guy was sitting at the bar alone and could have been waiting for someone you never know, but because he was alone, she said he was a loser with no friends that hates his life.

Completely killed the mood and I lost interest in her after that. Couldn’t see myself going on a second date with someone like that.

nine-koepfer-iPbwEiWkVMQ-unsplash-1024x683.jpgPhoto by nine koepfer on Unsplash

14. A Decade Later: Doing it Like an Alien in the Theater

When I was in 4th grade, a boy in my class came up to me and used his middle finger to rub the crease in the center of my plan. He said, “Do you know what this is?” When I told him no, he responded, “This is how aliens do it!” I ran away from him screaming, “EWWWWWW!”

Fast forward 10 years and I’m working at a summer camp. One of the camp counselors asks me on a date and said yes. We’re sitting in the theatre when he reaches over and starts “doing it like an Alien”. That memory from elementary school floods back into my memory and I immediately feel grossed out. He does this for THE WHOLE MOVIE. 

Firstly, the movie was very long. Secondly, it was one I really wanted to see! So I end up sitting there for almost 3 hours just so I could finish the movie. When we finally left, we didn’t go on another date.

jake-hills-23LET4Hxj_U-unsplash-1024x683.jpgPhoto by Jake Hills on Unsplash

15. The Quest for Love: A Man's Desperate Attempts to Find a Wife

He came to pick me up and when I got into his car, he explained that he delivered pizzas for a living so it smelled of pepperoni. No big deal, he’s making an honest living, right? He then turns on the car and the AC blasts out this horrendous smell. I couldn’t help but gag a bit between this smell and the pizza. Turns out, he had soaked paper towels in cologne and then shoved them into the vents. 

As we drive away, I’m silently gagging into my shirt and praying to God that the suffering will end. The plan was to get some ice cream, but instead, he pulls into a parking lot with a snow-cone shack and tells me I could choose any flavour I wanted. Wow, so lucky! Turns out his buddy owned the thing and they sat and chatted for what seemed like an eternity. We eventually get our flavoured ice and went back into the car. I told him I was ready to go home, but he tells me there was something super special that he had planned and to please let him follow through with it.

We drive up to the canyon and he parks. I’m positive I’m going to be the next missing person on the news at this point. Against all odds, I hoped that if I just appeased him, he’ll play nice and I’ll survive. We get out of the car and he walks me to the edge of the area. He pulls out…a bench from the bushes! A full-on bench, people! He explains he stashed it there earlier so that we could enjoy the sunset comfortably.

I sit down as far away as possible as he just kept scooting closer and closer until I literally fell off the bench. I tell him I’m not feeling well and that I should go home. As we drive back down the canyon, he asked me how soon I’d like to get married…to him! I told him I was 19 and had no intentions of marrying anyone anytime soon. At this point, he stopped talking to me completely. 

We make it back to my house and he walks me to my door. I thank him for the night and shakily try to get inside as quickly as possible. He suddenly grabs me and tries to kiss me. I pushed my hand into his face while screaming NO and kicked him as hard as I could. He stumbled down the porch with tears in his eyes and holding his crotch as I crashed through the front door.

Fast forward 2 or 3 years later and I hear him on the radio as a call-in. He’s bawling about never being able to find someone to love. And slowly, call after call of women called in to share their experiences with him on dates. Every single one of them had the exact same story! He legit thought that if he played this date out enough times, he’d find a wife.

thomas-park-FQF4OSws6Qc-unsplash-1024x683.jpgPhoto by Thomas Park on Unsplash

16. A Tale of Heartache: My Dating Disaster

Back when I was much younger and more meek, I planned a date with someone I met on a dating site. The person was traveling in from somewhere, I don’t remember where. But earlier that week, my uncle had passed away. I was a complete wreck. I contacted the person the day after when I was more coherent - this was also nearly a week before the scheduled date - and asked to reschedule because of the death. 

He refused, came into town, and I, being pathetic at the time, agreed to go meet him after he threw a bit of a fit. I felt bad because he had driven from about three or four hours away. The date was miserable for me. He even expected us to hook up which was NOT happening because you know, I was emotionally distraught. 

The date ended with him slinging insults at me. I decided to just leave. I drove around for a bit in case he tried to follow me, but then I just went home to be with the rest of my family like I had wanted to do in the first place.

mayron-oliveira-mibn6LLm9kA-unsplash-1024x683.jpgPhoto by Mayron Oliveira on Unsplash


17. My Unusual Date: When Conspiracy Theories and 45-Degree Angles Collide

I had an interesting experience the other day. I met someone online who lived 40 minutes away from me in a small, conservative town. I decided to take a drive out there, even though I wasn't sure what I was getting myself into. When I arrived, the date was filled with him spouting off conspiracy theories, all while he kept himself facing away from me at a 45-degree angle. I tried to step into his view once, but he immediately shifted himself away again. It was definitely an experience I won't soon forget!


18. The Worst Date Ever - A Cautionary Tale

After an excruciatingly long car ride listening to him discuss his love of clubs and bottle service, I arrived at the restaurant he referred to as 'enough of a hole-in-the-wall for a girl like me'. After ordering, he said he needed to check his bank account and then asked me to cover dinner. He then proceeded to explain his wild theories about the earth being flat and his plan to become a senator on Mars in 10 years. Then, despite my protests, he dragged me to a club where he asked me to list examples of why it was the worst date ever. After I called an Uber, he proceeded to text me asking for a date every day for a week until I blocked the number.

shawnanggg-nmpW_WwwVSc-unsplash-1024x768.jpgPhoto by shawnanggg on Unsplash

19. The Hike That Ended in Total Collapse: A First Date Disaster

I was the cause of a bad first date - or so I thought. I had grossly underestimated how long it would take my date (who was a really nice guy) to hike the 7 miles we had planned. As the sun went down, I had to call a friend to get the ranger hotline so we could let them know we were still on the trail after 9 when the gates closed. By the last three miles, my date was giving pep talks to his legs and threatening to eat the frogs that were hopping on the trail. I had to use my phone to light his way as it was pitch black and he hadn't brought his own. In the end, I felt really bad for my poor date - I had definitely not intended to walk him to the point of collapse!

toomas-tartes-Yizrl9N_eDA-unsplash-1024x683.jpgPhoto by Toomas Tartes on Unsplash

20. A Date Gone Wrong: When Naivety Meets Aggression

When he showed up, he was on the phone with his family talking about his new wife (me). By that point, we’d only talked for maybe 5 minutes. I had a few drinks trying to be polite, and I was honestly just trying to give him a chance. I was new to the city and he wanted to show me his apartment that he just bought, saying it would help me learn the costs, etc., etc. 

I was too nice and naive back then, and it was basically my first date ever. As soon as we got inside, he locked me in the apartment and shoved his tongue down my throat. I shoved him off me and unbolted the door as fast as I could. I ran as quickly as I could to the train station. He kept calling me after that wanting to go out again…

melanie-wasser-j8a-TEakg78-unsplash-1024x783.jpgPhoto by Melanie Wasser on Unsplash

21. Tinder Date Gone Wrong: Ruining Someone's Day One Margarita at a Time

She showed up 15 minutes late and spent the next 15 minutes staring at her phone, responding with a singular word for most things: “Yep”, “totally”, etc.

That is until the waiter arrived and she’s suddenly wanting to do shots before we get our actual drinks. She started asking, “Should we get 2 or 3 appetizers? Do you think you’ll want dessert?” I just ordered a beer while I looked at the menu.

As soon as the waiter leaves, she’s back on her phone with one-word answers. She then orders a HUGE dinner with 3 appetizers, a shot, and ANOTHER margarita (she’s barely been there for 15 minutes at this point). 

I gave it about another 5 minutes before I left for the “bathroom”, found the waiter, paid for my beer, gave the dude a $5 tip, and told him she was going to pay for her own food. I left after that. I honestly hope I ruined her day. She was clearly going on these dates just for a free dinner.

jarritos-mexican-soda-idP6ct9jkmk-unsplash-1024x683.jpgPhoto by Jarritos Mexican Soda on Unsplash

22. Two Tinder Dates Gone Wrong: A Cautionary Tale

I went on two dates that were both complete disasters. 

Date 1: I matched with someone online who was military branch redacted, but he was from the same general area as me. We went on a hike because both of us loved the outdoors. He proceeded to spend the date telling me about all the horrible things he’d seen on Search and Rescue missions. When I’d mention hiking or camping, he’d press the importance of “having a man in such situations”. He then talked about the trauma of being a virgin in the military. He quizzed me on my family’s religious beliefs because “there wasn’t much information on my Facebook”. I had not given him my last name AND my Facebook was supposed to be a private account. He went on to make a big deal about how I must have lied about my height because he was significantly shorter than me. To top things off, he tried to guilt me into bringing him along when I sent the code word to a friend to bail me out.

Date 2: I met up with a dude to go thrifting because hey now, it’s a public space. He started the date by getting angry at me for lying about my height on my profile because he was shorter than me. This transitioned into him pointing out the landmarks in town where a serial killer had scoped out victims, followed by him quizzing me about the “appropriate lengths of engagements”. He pointed out all the stuff in thrift stores that could be used as murder weapons or maybe had been used for murder and were being hidden in there. It was the perfect way to dispose of a murder weapon, apparently. I made many attempts to have literally any non-murder-based conversation. He kept proposing he gives me a ride and we go to a nice restaurant for dinner. That’s when I asked my friend’s brother to pick me up so I could get outta there.

siavash-ghanbari-viMyUbkD84k-unsplash-1-1024x683.jpgPhoto by Siavash Ghanbari on Unsplash


23. From A Date to the Movies to Pulling out Trash

Alright, I will try to keep a long story short. We were going to the movies but she got a call from her sister because of some sort of emergency. I should have left, but she asked me to come along and we could go to the movies after. Big mistake.

We get to her place and it is absolutely horrific. The most disgusting, hoarder, trash hole I had ever seen. I immediately called an Uber which was like 15 minutes out.

Next thing I know, her sister runs across the hall completely naked and screaming. My date called her mother who came home from work. The first thing the mother does is start screaming that the neighbours threw away some roofing tiles in the dumpster out back after she gave it to them a year ago. She claimed they were being “really rude”. She began pulling these disgusting, tattered, and totally unusable tiles out of the garbage and said to my date, “Why doesn’t your boyfriend help me?” As an aside, this mom smelled like old cat litter and looked completely crazy.

While all of this sent on, the sister was still naked and running around screaming. I hopped out of there just in time. Nothing will ever top this worst date for me.

jilbert-ebrahimi-b0p818k8Ok8-unsplash-1024x683.jpgPhoto by Jilbert Ebrahimi on Unsplash

24. Match.com Date Reminds Us That Profiles Aren't Always Accurate

I met a girl on Match.com who looked nothing like her photo. We went out for coffee and I quickly realized we weren't a match. She was in her twenties and had never been on an airplane or more than an hour away from her hometown. She was working at a shoe store, which I didn't even know existed until then. She asked me if I had any 'ink', and I could tell we weren't on the same page. She talked about motorcycles for a while, but I couldn't relate. It wasn't a terrible date, but it reminded me that you can't always tell how compatible you'll be with someone just by looking at their profile.

austin-distel-2vCqH34PqWs-unsplash-1024x683.jpgPhoto by Austin Distel on Unsplash

25. Love at First Sight? Not Quite...

I was 19 or so sitting at a bus stop bench waiting for the bus to go to work. This stunning woman sits next to me. Not long after she starts talking to me. We have a pretty good conversation and I build up the courage to ask if she'd like to meet up sometime at a nearby coffee shop. She says YES! We agree on a day and time then the last thing she says to me before I get on my bus is, "It's a date."

I go to the coffee shop at the agreed time and see she is already there. She has a male friend sitting right next to her. No big deal, I figure he must be there in case I'm a creep or something. I sit across from her and we order a drink. Then right away she says, "So, what do you think about Jesus?" and pulls out a pamphlet. I reply, "I thought this was a date." She says something along the lines of, "I didn't think you'd show up if it wasn't." I ended up leaving right away before she had a chance to see me tear up.

yannick-pulver-FAU2NI1Uixg-unsplash-1024x683.jpgPhoto by Yannick Pulver on Unsplash

26. Hot and Heavy Make Out Session at the Night Club

Met a girl at a night club and we didn’t know more than each other’s names before we started making out. The next day, I decided to call her and ask her on a proper date to get to know each other. I suggested we walk around downtown and look at Christmas lights. Romantic, right?

Well after about a half hour of walking around and talking, she turns to me and says, “This is not a date. We are not on a date.” Well, that came out of nowhere.

Disappointed, I said I wanted to end the night. I told her I’d walk her to her car though. Once we got to her car, she attacked me, sexually speaking. I was into it so I went along. We took the hot and heavy make-out session inside her car, out of the cold and snow. About two minutes into kissing, she yelled out, “I LOVE YOU!”

I noped out of that one right away!


27. The Worst Date Ever: A Baseball Game With a Princess-Type

I took a woman to an MLB ballgame as a date. She was a friend of a friend. She turned out to be the “princess-type” personality which was pretty immature, especially for her age. She kept making snide remarks such as saying we should have parked valet instead of parking in the stadium lot. She also said our seats sucked because they weren’t directly behind home plate. We quickly ran out of conversation topics after the first inning, but there were eight more innings to go. I should have pulled the plug in the second inning, but we stuck it out for the rest of the game.

joshua-peacock-ae4KypxWHr8-unsplash-1024x683.jpgPhoto by Joshua Peacock on Unsplash

28. My Clumsy Date: A Story of Embarrassment and Toilet Clogs

Met a guy I had emailed back and forth with for a while. Circa 1999-2000. We had a nice dinner together and he invited me back to his place. I was newly divorced with zero dating experience, but I decided to go to his house. We drove separately though. His house was in an OK area and he had a job with a well-known accounting firm. He barely had any furniture inside except for a folding chair, so we sat on the floor and talked. He had one floor lamp that was tinted pink around the bottom part of the glass covering. He explained his family owned a funeral home and that it was from there - supposedly the pink light makes the bodies look better.

At some point, I really needed to use the toilet. It was…not good, and I clogged it up. I prayed for death to take me while I waited a minute before trying the flush of desperation. It failed. I looked everywhere for a plunger but couldn’t find one. 

So what did I do? I went to chat with the guy for a couple of more minutes before saying my goodbyes. He even called me to make sure I got on the highway okay, obviously before he discovered what I’d done. I hated myself for doing it, but I didn’t know what else to do! 

We never spoke again after that.

jas-min-egqR_zUd4NI-unsplash-1024x683.jpgPhoto by Jas Min on Unsplash

29. At 18, I Asked a Girl Out on a Date - With a Background Check Involved!

At 18, I asked a girl to go to the drive-in theatre with a group of people. She told me her dad said no, but that I could go to her house for a movie instead. I randomly picked one up and thankfully it was PG because the dad asked what I brought over. 

To make sure I was up to no mischief, her dad had his police buddy run a background check on me before we could watch the movie. While we waited, I got the entire “What are your intentions with my daughter?” talk. I passed the background check and we watched the movie, but I sat on one end of the couch while she sat on the other. There was a rack of guns on the wall behind us and her dad was in the next room. 

When the movie ended, I politely said good night to her and her dad and still had time to make it to the drive-in with my friends. I never tried to date her again.

jens-kreuter-ngMtsE5r9eI-unsplash-1024x575.jpgPhoto by Jens Kreuter on Unsplash

30. My First Date with a Strange Ranger

He took me to an Italian restaurant. After we ordered, he got a phone call and had a small chitchat with the person on the other line. Then he said, "Mom, I know, I ordered the cheapest thing on the menu. Mom! I'm here with my date. I'll tell you how much the bill was afterward." It was a first date and I soon realized he was living with his mom, who micromanaged all of his money - to the point of calling during dinner to see what kind of money he was spending. Super creepy, really weird. I saw him one more time to confirm he was a strange ranger and broke it off. After that, I had a good laugh about the whole situation.


31. My Date to the Surprising Art Gallery: A Tale of Objectification and Melting Clocks

Years later, I was planning a second date with a woman I quite liked. I asked her if she wanted to go to an art gallery and then out for a meal. She said yes. We ended up going to a rather famous gallery in London that was doing an exhibit on Dali and a few others. It sounded like a great idea to look at some stupid pictures of melting clocks, and then laugh about it over food. Except, Dali also had a lot of WEIRD fetish work. Apparently, he was heavily into literal objectification, as in naked women AS furniture and other objects. It was a guided tour, and everyone else there seemed to know and enjoy rather too much what the “art” was all about. By the time we got out of there, the rest of the date was just me trying to explain over and over again that I had no idea what it was about before going in.

dannie-jing-3GZlhROZIQg-unsplash-1024x768.jpgPhoto by Dannie Jing on Unsplash

32. My Worst Date: The Date I Didn't Realize I Was On

My worst date was a date I didn't realize I was on. I lived in Korea for a few years and wanted to practice Korean. I made an online ad asking for someone to help me with my Korean, and I'd help them with their English. Lots of people responded, and I hung out with them one by one looking for who was the best teacher and who I got along with. 

One of them wanted to meet in a coffee shop. I get there and meet her. She was super quiet and really awkward. She'd barely even look at me. I'd say something in Korean, and she'd respond in English. I asked her if we could talk in all Korean for a while and then all English later, and she simply didn't respond at all. Sometimes she'd just sit there quietly for a minute or two after I asked something, and I'd just change the subject. 

Eventually, I gave up and said I was leaving. She said she was leaving too, then. As we were walking out, she asked if I wanted to get a beer now. I tried to say no as politely as possible. She asked when we could go out again, and that's when I realized she thought this was a date. A terrible, terrible date. On the plus side, I met my wife with that same ad. Neither of us thought *that* was a date, but we did eventually end up dating.

daniel-bernard-qjsmpf0aO48-unsplash-1024x684.jpgPhoto by Daniel Bernard on Unsplash

33. The Worst Wingman: A Tinder Date Gone Wrong

This was the second date I went with this guy I met online. I wasn’t particularly into him, but he was nice enough and I was new to the area and looking to meet people.

At the last minute, he says his buddy just got to town and asks if he could tag along. I said sure. They came over to my place first, then we went to a dance club. His buddy was awful from the start, but it only got worse. He insulted my house, my driving, my job, etc. He clearly just wanted to hang out with my date and didn’t like that I was there.

At the club, he kept trying to dance up on girls who were obviously not into it. He’d scream in their faces when they asked him to stop. My date had totally disappeared trying to be a wingman for his rude friend. After an hour, I’d had enough. I found my date and told him he could come with me or he’d have to find another way back to his car. He’s sulky but agrees.

We get back to my house and my date apologizes for running off and begs to come in, promising his friend will behave. I relent because I’m an idiot. Within 10 minutes, it became painfully obvious that, having struck out at the club, my date is now trying to get me to sleep with his friend. I kick them out immediately. He texted me the next day calling me a baby and accusing me of stealing his phone charger.

antoine-j-A_0C42zmz1Q-unsplash-1024x683.jpgPhoto by Antoine J. on Unsplash

34. The Most Hilarious First Date Story Ever!

This worst date story is totally on me. Here goes.

High school, was the first date of my life, super nervous. (Is the scene set yet?)

Took her to a “fancy” dinner. At every pause in the conversation, I would gulp water. Because awkward, nervous, uncomfortable silences can be momentarily filled by drinking water, right? Probably had about seven big glasses of water during that dinner.

Then we went to the movie theatre. Decided to sit in the last row, right in the middle. Pretty packed place. Well, as you can imagine... I needed to pee. A lot. I probably got up to go about (at least?) FIVE times during the movie.. had to slide down the whole row to get out, the dude next to us was super annoyed but also chuckling under his breath about it. Needless to say, did not have a second date. Would love to hear what she was thinking now.


35. My Cringe-Worthy Dates with Writers: A Story of Uncomfortable Realizations

I went on a second date with a guy who initially seemed really great. Halfway through it, he tells me about some stories he's written. I'm also a writer so I was very interested. He goes off about his story about women in the slave trade, in deep detail. He then tells me another story (which luckily I can't remember) but it was also about abused women in some sense. I was uncomfortable but I asked him why he chose such topics. He said it was just for fun. I got a weird vibe from the guy after that so we did not go on another date.

At a different time, I went on an ice cream date with a guy. We talked as we ate and the conversation went from normal to him talking about the decline of his mental health for a good few hours. I felt bad for him because he obviously needed someone to talk to but at the same time...this was a date and not a therapy session. The guy had some things to work through and probably shouldn't be dating. That was our only date. I'd like to add that both of these guys were 'writers' which is why I no longer go on dates with other writers.

unseen-studio-s9CC2SKySJM-unsplash-1024x683.jpgPhoto by Unseen Studio on Unsplash

36. Tinder Nightmares: Tales of Woe from the Dating Scene

I’ve had a few bad dates but the worst would probably be this cute blonde from Tinder. We had texted for 4 days and she seemed intelligent and interesting. We arranged to meet up at a karaoke bar for drinks, chatted, and maybe a little shared humiliation. I got there first and decided to wait at the bar. I’m chilling there, slowly sipping on an old-fashioned when my Tinder date rolls up and shouts, “Oh my god, are you Andy?!” then shoves her tongue down my throat while I’m trying to answer.

At this point, I’m thinking, “Okay…not a ‘take home to mom’ kinda girl, but we can probably have a bit of fun.” I suggest we find a table and she says, “Sure, let me just get a drink first.” The Tinder chick orders 4 shots of tequila while I’m in the process of thinking to myself, “Starting our date by sharing shots, ballsy.” 

This tiny, cute little girl slams all four shots of tequila in a row like something from a sleazy 90s frathouse movie. I was honestly reeling from this chaotic energy that just waltzed into my life like a hurricane but figured I would feel the situation out a bit more. She actually leveled off for a while and we had some good laughs, if not an entirely shallow conversation.

Then it was time to do karaoke. She gets on stage and apparently decides to “remix” the song by singing it in an offensively stereotypical bad accent, shouting all the racial slurs she knows. It might be trashy but borderline acceptable in a tight-knit group of friends where everyone is comfortable with each other, but I’m clearly mixed ethnicity and there’s a diverse crowd in the bar. People were definitely looking around and starting to get upset. 

I shoot her a quick “Yo, what the hell” thinking maybe she was too drunk and needed reigning in, but she waved me off and double down on her racist show-and-tell. This was the one and only date I’ve legitimately run away from. I didn’t even try to split the bill, I just bolted and left her to deal with it.

brandi-alexandra-UqEJ1ojVXOY-unsplash-1024x576.jpgPhoto by Brandi Alexandra on Unsplash

37. Never Give Anyone a Chance: My Myspace Date Gone Wrong

Back in the days of Myspace, there was a guy who contacted me. He wanted to meet up, which was cool, but he also wanted me to pick him up, which wasn't cool. As I was young at the time, I didn't want a stranger in my car. After a bit of back and forth, we eventually settled on meeting at the mall. When I got there, he wasn't there yet, so I waited a bit before he showed up. He asked if I had been waiting long, and being polite and wanting to make a good first impression, I said no. He called me a liar, which I was taken aback by, but I figured it was his way of joking. Throughout the 'date,' he kept telling me I was lying, stupid, and an idiot over small and insignificant things. Eventually, I had enough and left, and he sent me a message over Myspace saying he was 'too spicy' for me. I blocked him and that was the end of it.

hua-thun-ho-9IanjYPeoLU-unsplash-849x1024.jpgPhoto by Hua Thun Ho on Unsplash

38. Two Dates I'll Never Forget: My Night of Horrors

It was a night of two dates that I won’t be forgetting in a hurry. One guy was about 10 years older than his photos and he downed his drink in seconds. He was twitchy as hell and went out for so many cigarettes, I think I counted four in half an hour. The conversation was also so bad. When we talked about books and I told him I liked to read Orwell, he said, “Oh my god a girl that likes good literature, you’re so perfect." Gross.

Number two was so clingy. It was our first date and we had been speaking for perhaps a week. He wouldn’t let go of my hand at the table and stared at me nonstop, really creepily. When we left, he grabbed me (quite forcefully) and kissed me in the street clearly thinking he was romantic, but it felt more like sexual assault. I had been refuting his advances all night but he wasn’t getting the picture.

freestocks-RgKmrxpIraY-unsplash-1024x683.jpgPhoto by freestocks on Unsplash

39. An Unexpected Adventure: A Single Dad Date Story

I'd been talking to this guy and we finally decided to go on a date. He said he'd take me out for dinner and drinks. He offered to pick me up after work so I said okay. He sent me a text saying "WE'RE" on the way. I immediately asked, "Who is we??"

Well, he's a single father and his sister was supposed to be watching his 4-year-old son, but something came up. Uh... Okay, I still went along with it. So he said he wanted to go home to shower first since he was in his work clothes. We got to his house and he showered and fell asleep for like 4 hours while I hung out with his child who smacked me in the face TWICE. After I told him not to do that anymore, we ended up getting along and having fun. Turns out, he's a sweet kid. He finally woke up and we ordered pizza. I took an Uber home. I would have left before he woke up, but I didn't want to leave his kid alone. We had an unexpected adventure and it was a great experience overall!

yuri-shirota-p0hDztR46cw-unsplash-1024x679.jpgPhoto by Yuri Shirota on Unsplash

40. Date Gone Wrong: A Humorous Account of an Unfortunate Bumble Date

Went on a date with a guy from Bumble and it was so bad I have to put it into bullet point form.

  • He took me to a restaurant and when the waitress asked for my order, he put his hand out to cut me off and said, “She’ll have a salad."
  • He got shots for us even though I told him I didn’t want him driving under the influence. He put on a gaudy gold watch when we got into the car and said, “Cause I gotta let 'em know!”
  • He got us front-row tickets to a baseball game and wanted to be on the big screen so he got on his seat and twerked every 10-15 minutes. He was in the army and his lead happened to be sitting just a few seats down. When my date went to the bathroom, the two ladies behind me asked if I was okay and if I felt safe.
  • He then takes me to the beach after the game and dropped everything. It was cold on the beach so this man says, “You can put your hands on my chest,” and proceeded to put my hands under his shirt on his chest. He then tells me about all the girls he slept with at my university and told me if they were good or not. He was convinced girls didn’t date him because he was short (he was about 5’4). A few days after the date, he sent me a video of him singing (poorly) and shooting off a gun/using the gun as a beat against his desk. This date was so wrong in so many ways.

hhh13-tEMU4lzAL0w-unsplash-1024x680.jpgPhoto by 傅甬 华 on Unsplash

41. Date Gone Wrong: Robbed and Dipped

I went on a date and ended up at a hotel. We made love, went to sleep, and when I woke up, he was still there and everything seemed fine. I went outside for a smoke and he asked me to get him coffee from the lobby, as the coffee pot in the room wasn't working. I got the coffee, and when I returned, he had robbed me of all my cash, phone, and cigarettes. I called the cops on him. A month later and I still haven't heard anything from the cops.

On another bad date, a guy drove off after dropping me off at a grocery store. I was in the store for less than five minutes and he just left me there. I had to walk an hour home after 11 pm, and on the way, a strange man assaulted me. I cried the rest of the way home.

vojtech-bruzek-Yrxr3bsPdS0-unsplash-1024x683.jpgPhoto by Vojtech Bruzek on Unsplash

42. Deployed Overseas, Home for a Date with Heartbreaking Results

I was deployed overseas in the early 90s. When I came home my family was telling me about my little sister's older friend. I should stay away from her. My sister didn’t plan anything with her while I was home. The friend had recently and suddenly lost her fiancé - he choked on a bone at Thanksgiving Dinner.

So I think nothing of it and go on with my visit home. Mom and I are getting lunch and this woman is approaching our table. We lock eyes. She has a wry smile. She says hi to my mom and my mom looks at me awkwardly and introduces us. I recognize the name. That combined with mom's subtle awkwardness let me know this was the friend I was told to leave alone.

She asked if I needed company while I was home and that we should go out. Right in front of my mom! I didn’t want to be rude so I said sure. I told her to my mom’s house later and we’ll figure it out (didn’t have my first cell phone until a few years later).

So the go-to date spot in my hometown was the movie theater. I had been out of the country and there was no Internet, so I had not seen any movie trailers. I picked a Tom Hanks & Meg Ryan movie. Romcom has to be a great choice right? Sleepless In Seattle it is.

For those that may not remember that movie, the whole first part is Tom Hanks lamenting the loss of his lady. This chick just lost her fiancée. She was BAWLING. I suggested we leave, but she insisted we stay. She said she needed this but I felt so bad. She ended up CRYING through the WHOLE movie.

As we were leaving I was continually apologetic. I was planning my escape to get home but she suggested we get a drink back at her place which was the house she shared with her fiancé until recently. On the way there she explains that she knew he had been cheating on her with a girl from his work.

As soon as we get inside she pushes me against the wall and starts going to town on me. She was aggressive and strong and had my guy out in no time. We started getting intimate right there and then. This kept going on for a couple of days, almost constantly. She would cook a couple of things here and there, but then we were right at it again. Part of it was the conversations were too damn crazy. The best way to stop talking was to just start doing it again.

After two days away, my mom called and asked if I was going to spend some time with the family before I had to go back. That’s what got me out of there. We talked on the phone a bit and snuck one more session in before I left. We shared some great intimacy, but it was a horrible date. And I was a jerk for leaving the fam for a couple of days.

julien-andrieux-Ei0V7r0vcoY-unsplash-1024x576.jpgPhoto by Julien Andrieux on Unsplash

43. Valentine's Day Fiasco - A Tale of Unrequited Love

I was 15 and this guy asked me out on Valentine's Day. This would have been my first date ever and I was so excited. We texted and talked a lot for the past three weeks and had only met up twice since we were both from different schools. Feb. 14 comes and I was so excited I came 30 minutes earlier than the agreed time. After 30 minutes, no show. I thought, "Okay, maybe he's just running a bit late." So I waited and even sent him a text twice asking where he was.

2 hours passed and still no show. I actually tried calling him but he could not be reached. I went home crying. That night he called explaining his friend dragged him to his house along with his group mates to finish a project. To be honest I would have understood. But what really ticked me off was that he could've at least sent me a text telling me that he couldn't make it. That really put me off dating.

laura-ockel-zAOBpEE_vV4-unsplash-1024x701.jpgPhoto by Laura Ockel on Unsplash

44. My First Online Date: An Unexpectedly Informative Experience

My first online date was informative, as I learned why some women only post pictures of their faces. She was extremely overweight. Furthermore, she was only in sweatpants and a sweatshirt. All this is minor, compared to what happens next. After making some small talk, I ask her how her day was going. She asks if I really want to know and I mistakenly say yes. She launches into a rant about how she got fired from her last job because people were plotting against her. A new job she signed up for was just a scam that stole her credit card information. She just got out of an abusive, physical-only relationship. Her 25-year-old sister was abandoning the family to move to New York City. She was just kicked out of school because people said she was plotting to kill someone, but she swears she wasn't. "People are always plotting to get me, it seems." I was too frozen to leave at that moment and stayed for about another hour trying to make the most awkward small talk ever.

pratik-gupta-CNOo9ZMBqRM-unsplash-1024x683.jpgPhoto by Pratik Gupta on Unsplash

45. My Awkward Date Night with a Drunker Than Expected Coworker

About ten-ish years ago, I went on a date with a coworker who seemed like a nice, low-drama kind of guy. He asked me to go out to a bar and while I'm not a big drinker, I agreed. To my surprise, the guy got messy drunk to the point where he couldn't drive home. Since he had driven us there, it meant that I, too, was out of a ride home (this was pre-Uber days). The guy was drunkenly adamant about wanting to walk home as he lived maybe three blocks away from the bar. We had to walk past the police station, and as we passed it, he stopped, started screaming about hating the cops, and ended up puking on the sidewalk outside the station. He then sat down on the sidewalk and refused to keep going because he didn't feel good. I ended up leaving him there, finishing the short walk to his house, and getting his roommate to take me home. The roommate confirmed it was a pretty normal thing for the guy to get stupid drunk any given night. There was no second date and work was awkward for a while.

qui-nguyen-Zrp9b3PMIy8-unsplash-768x1024.jpgPhoto by QUI NGUYEN on Unsplash

46. The Heartbreaking Story of a Perfect Guy and an Impossible Choice

I was 19 and met this guy online through a dating site. We talked off and on as friends for months and I thought it was strange that he never shared a pic, but it wasn't a big deal. We agreed to meet and he was perfect in every way, except that he was a big guy, over 500lbs. He had a hard time walking and I just wasn't attracted to him. He told me he didn't have a medical condition, and had no intention of changing. After the date, I went home and cried. He was perfect, but I said no because I just couldn't do it. I tried to keep being his friend, but he wasn't interested. It was really awful.

m-T9THJMIIMPM-unsplash-1-1024x682.jpgPhoto by M. on Unsplash

47. Dating Mayhem: A Snowy Night of Drama and a Broken Leg!

Went to a small but popular place that wound up being packed, so we shared a booth with another couple. My date started hitting on the other guy---who responded. His date and I are rolling our eyes at each other like, "What the hell?"

When we left, it started snowing. My date slips and falls and then can't really walk, so I'm carrying her down the sidewalk back to her house. She sees an SUV creeping by in the snow (about 3-4" by now, which is a lot for Virginia), hobbles over, and starts banging on the window asking for a ride. SUV nopes out. I carry her home (fortunately she was petite, although that probably contributed to low alcohol tolerance [plus it later turned out she was on antidepressants, not a good combo]) and I'm asking if she needs to go to the ER because I can call a cab (I didn't have a car).

She starts yelling, "JUST GET OUT!" I write down my number and tell her to call me if she needs to go to the hospital, and she flips to, "You're just gonna leave?" Then back to, "GET OUT!" Then flip-flops a couple more times. Finally, I escape. A week or two later I go out with my roommate to a different place for a couple of beers, and there she is at the end of the bar.

"I BROKE MY LEG!" Big cast/splint from ankle to hip. Said I hoped she got better quickly and we bolted. And no, I didn't wind up dating the girl from the other couple in the booth.


48. Dinner Date Disaster: How I Saved Myself from an Unbearable Date

I went on a dinner date with a guy I met on an online dating site. He takes me to a tapas restaurant and proceeds to chug 3 drinks in a matter of 15 minutes. The waiter asks if I want to see a menu and he tells them no. So apparently dinner is not happening. This guy sucks and he keeps randomly interrupting me to tell me where he buys his clothes. So I excuse myself to use the bathroom and the wait staff pulls me aside and asked me if I needed help because it was looking bad. They said they will tell him I left and to stay in the kitchen until he leaves. I waited 10 minutes until he left and I went to Wendy's for a spicy chicken sandwich.

adrian-swancar-7Ssnka8OqLM-unsplash-1024x768.jpgPhoto by Adrian Swancar on Unsplash

49. Never Again: A Story of Getting Too Close For Comfort

I was out at a coffee place when I met this friendly guy. We decided to meet for coffee once more and then went for dinner at a bar. Things were going great until he decided to lick my face! I was so shocked I could hardly move. He then tried to playfully poke me to make me feel better, but I asked him to stop. He then leaned in and whispered, "I'll just poke your sleeping body later."

I was so scared I asked the bouncer to stay with me until I could get away from the guy. A few days later I received messages from him saying he was worried about me and was going to "stop by my parents later to see if I was okay". I had never given him my parent's address and told him I would call the police if I ever heard from him again. Thankfully, I never heard from him again.

jonas-jacobsson-1iTKoFJvJ6E-unsplash-1024x683.jpgPhoto by Jonas Jacobsson on Unsplash

50. Girl Dates Guy Thinking He's Indian, Gets Scared of Hispanic People

I had been texting this girl and she was really digging me. I was in school for accounting and she LOVED that. Apparently, she was tired of all these artsy guys. So we go on a date. Her family works in high finance in Singapore and is really well off. I'm asking her about competition with Hong Kong, SK, and Taiwan. She tells me a little but then ask me about the industrialization of India and if I had seen any changes. I'd never been so I tell her I didn't know. At this point, she is confused and asks me why I've never been to my homeland. I tell her I'm American and my parents are Mexican. Her eyes got so wide. She suddenly gets super awkward and says I'm lying. She wants me to prove it so I show her my ID which shows I have a Spanish last name. She gets super uncomfortable and tells me to take her home. I'm like, what the hell?! So I take her home and she is visibly scared. The longest 20-minute drive of my life. I drop her off and that was the last I ever heard of her.

emir-saldierna-oHWCOXSYdsg-unsplash-734x1024.jpgPhoto by Emir Saldierna on Unsplash

51. The 'Sympathy' Date: A Cautionary Tale

Went to a bar because he wanted to watch the MMA fight. Got there and had a casual conversation, but he kept looking at his phone and heaving these overly dramatic sighs. I finally asked what was wrong and he said, "I didn't want to bring it up but my ex-fiancé was killed in a plane crash today." Cue up the 'omg, so sorry' with a bit of skepticism. When the fight finished, he got our (separate) checks and then said he'd walk me to my car.

When we get there, he says, "So. You coming over to make me feel better or what?" Mmm no, sorry, hard pass. A Quick Google search upon arriving home revealed no plane crashed anywhere that day, which isn't to say there wasn't one, but I would put a lot of money into guessing there probably wasn't one. He texted me the next day to say he had a good time but it was a shame I was such a buzzkill.

andrew-palmer-_1REcmACJaQ-unsplash-1024x683.jpgPhoto by Andrew Palmer on Unsplash

52. A Smelly Date Night: When Dogs Interfere With Romance

I met a guy on a night out and he seemed interesting. He invited me out for Chinese food and a movie, but insisted I come by his house first to meet his four dogs. Not liking his dogs would be a deal-breaker for him. Cool, I love dogs.

I followed directions to his house, which was a mobile home with a small fenced yard. I expected the dogs to be small, but they were four large, mannerless dogs living inside the mobile home and the smell was completely encompassing. Turns out "dinner and a movie" meant watching one of the thousands of VHS tapes and DVDs he owned while he tried to get my clothes off me. All while four big dogs bounced around. I declined his kind offer of incredible lovemaking and got out of there. My clothes went directly into the washer after that and my car smelled like dog for days.

pauline-loroy-U3aF7hgUSrk-unsplash-1024x683.jpgPhoto by Pauline Loroy on Unsplash

53. My Unfortunate Dating Experiences: When Biology and High-Fives Don't Mix!

I was 28 or 29 years old at the time. We'd been talking for approximately 10 minutes over one drink when he asked me a question that took me by surprise: "So do you want kids? Cause if you do, you don't want to wait too long. You're drying up. It's biology. Don't be mad." I was so taken aback by his bluntness that I didn't know how to respond.

Then there was the time I met a guy for coffee, it was like 9 or 10am. The coffee shop was busy but fairly quiet. He'd ask me a question, I'd answer, and he'd loudly exclaim, "Nice!!! High five!!!!" He did this like 4 or 5 times before I had to tell him to stop because I didn't want to keep high-fiving. All I wanted was a nice conversation!


54. My Terrible Date with a Teaching Assistant

In my freshman year of undergrad, my TA for a comp sci class I was taking asked me on a date. He seemed normal/nice enough so I agreed and we went to dinner at a random restaurant in the city. He ordered for me which was not my favorite, but I was like "whatever" cause he seemed to know the place really well.

Turns out he was a narcissistic weirdo and talked about himself the entire time. He kept asking me/telling me to “pay attention.” He told me all about his ex-fiancé and basically went on a rant about how white women are so entitled so now he’s only interested in “black queens.” It was making my skin crawl; I felt physically ill.

At the end of the date, I wanted to split the bill. He said he would pay since I’d be paying him later *wink wink*. I didn’t even know what to say or do so I just stared at him and excused myself to go to the bathroom. I left through a side door. Luckily there were only two weeks left in the semester so I only saw him again for the final.

kenny-eliason-1-aA2Fadydc-unsplash-1024x683.jpgPhoto by Kenny Eliason on Unsplash

55. The Worst Date: A Navy Medic Brags About Suicide and Self-Harm

I went out with a guy who was a medic in the Navy. He looked nothing like his pictures, but I carried on out of politeness.

Over the course of the next three hours, he bragged about all the people he knew who had successfully ended their own lives. Bragged about how many times he had encouraged suicidal people to end themselves and how he had often self-harmed with them.

To make things worse, he worked in the hospital and was telling me how he would give depressed patients sharp objects and tell them that it was less paperwork for him to do if they just ended themselves. He also didn’t have a clue about most medical conditions and would just send people away telling them they were fine.

He finished off the date by telling me about his really messed up family and how his two 13-15-year-old brothers had been arrested for stealing and burning cars. AND his sister kept trying to stab all the family members. 

Suffice to say I made a swift exit and never met him again.

michael-afonso-BQgAYwERXhs-unsplash-1024x683.jpgPhoto by Michael Afonso on Unsplash

56. Drugged Up Date - How One Man's Impression Was Ruined By Wisdom Teeth Removal

I was really excited when I got a girl's number and decided to take a chance and ask her out. I went to the dentist a few days later and before I knew it, I had 4 wisdom teeth removed and was completely out of it from the anesthetics they gave me. Apparently, I told the dentist my date's number as my emergency pickup. I don't remember any of it, but she must have taken pity on me because she showed up at the dentist's office, drove me to the pharmacy to get my medication, and then dropped me off at my apartment, where I passed out. Unfortunately, that was the first and only time we ever went on a date. I guess I didn't make the best impression! I'm still trying to figure out why the dentist's office asked me for a pickup number while I was drugged up, but I guess my primary contact wasn't available.


57. A Night of Margaritas, Dancing, and a Confusing Date

I went out one night with some of my girlfriends. I was the young, naive girl in our group. We went to this bar that is on a lake and had a great time drinking margaritas. I met a guy...we danced, laughed, and just really clicked! My girlfriends were ready to go but I didn’t want to. He was making promises that he could get me home, but the DD in our group put her foot down and said we had to go. We exchanged numbers and made promises to talk soon, and the DD took us girls home.

The next day, I got a text from him! I was so excited because he had to be interested if he texts the next day right?! We make plans for dinner and he offers to pick me up.

Him: “So, pick you up at the same address?”

Me: “Same address? What are you talking about.”

Him: “The house I dropped you off at.”

Me: “You didn’t drop me off?”

Him: “Shut up. We did it in your driveway.”

Me: “Umm...no, we did not.”

Him: “Yes, we did!”

Me: “I’m really confused. And I think you are too...but I’m not the girl you went home with last night.”

So the date died before it ever got started. Grateful for the DD though! She was a lifesaver.


58. Date From Work Goes Horribly Wrong in Humorous Ways

Went out on a date with someone from work who I didn't know very well. Little did I know, he was a real jerk in many ways and was already drunk when I showed up. To add insult to injury, he started rudely heckling the small cover band that was playing in the bar. The singer stopped and said, "I'll give you $10 out of my own pocket if you can tell me this girl's name," and you guessed it, he completely blanked on my name in front of a whole crowd of people. To add the cherry on top, the next day he texted me saying, "You can try again," as if I was the one who had messed up.

karl-hornfeldt-n9HXLrsjnE0-unsplash-1024x683.jpgPhoto by Karl Hörnfeldt on Unsplash

59. A First Date Gone Horribly Wrong

So, it's a fairly quiet night and it's pretty early, and I have a reservation at 6PM for 2 people. A young guy shows up for that reservation about 10 minutes early and tells me he's very nervous as he's on a first date, and hasn't been on many of them. All that kind of jazz, kinda sweet really. Anyways, I seat him, and the girl arrives, like, 30 minutes late. She then proceeds to get extremely drunk.

About halfway through the meal, she answers her phone, takes the call, and starts talking about her date, right in front of him! She kept saying stuff like, "He's not really my type, I don't exactly like him but I figured I had nothing else planned tonight so why not." The young man looks super discouraged, pays his bill, and leaves. He's a nice lad, I've seen him a few times at the bar I work at now.

nick-rickert-bwq_f_JGKvg-unsplash-1-819x1024.jpgPhoto by Nick Rickert on Unsplash

60. Dodging a Bullet: How I Survived a Weekend with a Narcissistic College Friend

I had an old college friend come to visit me and stay for a weekend. I knew her in college and I remember her being amazingly intelligent and fascinating. Years later, I got Facebook and she was one of the first people to find me.

Both of us were single so she asked if I wanted to date her. I said hell yes! I was thrilled at the prospect. Unfortunately, the date went horribly.

  • The entire weekend was spent listening to her narcissistic stories. 
  • She told me jokes that were as old as the internet, reworded to sound like personal life anecdotes.
  • She told me all this insane edgy stuff she used to do or still does, like taunting the police (back in 2009) or sneaking Cuban products back to America when the embargo was still in place.
  • She tried to start a fight with a bouncer when we went to a bar and she forgot her ID back at my house (a block away).
  • We visited some of my best friends, and the moment we parted, she trash-talked them non-stop.
  • My brother came by since I texted him I was out and he hung out with us. She talked to him for quite a while. When he left, she then spent the rest of the night talking about how attractive he was. At this point, I was just counting the hours until she left. I was no longer interested in her.

When she FINALLY left, I get a text that night that said: “You failed all my tests. You laughed at my jokes that weren’t really jokes. You didn’t defend me against the bouncer, and you aren’t interested in my passions. You also just sat there and took it while I talked about your brother. Also, I don’t find you physically attractive.”

I didn’t reply; I just cut my losses and went to sleep. Several months later at 4am, I received another text for her. Same text as the one I just wrote, only this one was out of nowhere. I gave her absolute hell for it and blocked her on Facebook. She then made duplicate accounts and threatened me on those ones too. She gave up eventually, but boy, did I dodge a bullet.


61. A Date From Hell - The Worst Date Story Ever

I matched with this guy online, and he offered to take me out to dinner. I thought that sounded nice so later that night, he picked me up. We were driving and he asked me where I wanted to go. I told him I was fine with anything. He said, "Okay then," and pulled into a Subway. He then told me that he wasn't hungry, but that I should eat! So he stood outside of the Subway and watched while I went in and got myself food.

At this point, I was already mentally done but I wanted to see how much worse it would get. Spoiler, it got so much worse.

So I'm sitting in the car with the stupid sub on my lap, and he decided that it was a great idea to drive around, specifically through a dark, isolated ravine that was nearby. He drove for about 10 minutes into the ravine, parked the car next to an abandoned tennis court, and said, "Okay, you can eat now." I was just thinking, "I really don't want to die here," so I choked down the soggy sub while he stared at me. The second I was done, he pulled the car out and drove me back home. I was so grateful to make it home in one piece that it took me several days to process how messed up the entire date was. The cherry on top, at 2am that night, he came back to my house uninvited, carrying a bag full of stale donuts, and asked me if I wanted to make love (but it had to be without a condom since he didn't have any).

mae-mu-GIUc-l74UT8-unsplash-819x1024.jpgPhoto by Mae Mu on Unsplash