Work at a bubble tea restaurant right near a college. It’s a nice hangout spot with dim lighting, comfortable furniture, and board games. A lot of first dates happen here. Probably the worst I’ve ever seen was this guy that looked somewhere between 17 and 19 years old who met up with this girl around the same age. They got teas and took a seat at a table and played a board game and talked.

His mother sat at the table next to him the entire time and just stared them down. It made me feel so bad for him, but the icing on the cake is when she goes up to them at 8:30 and tells them that it’s time for the two of them, her and her son that is, to head home. The guy is visibly mad but says goodbye to her and follows his mom out.

Girl comes up to order another tea and I asked her about it. She was more than happy to fill me and the other girls in. This lady had essentially injected herself into the date, interrupting their conversation and critiquing her son’s behavior.

This isn’t as bad as some of the others but the guy and girl arrived separately and it seemed like they were meeting for the first time at the restaurant. They sat down then the girl excused herself and went to the bathroom. The guy ordered drinks for them both while she was gone then, after like 30 mins, ordered two meals. It was so obvious she wasn’t coming back but he kept calling her and eventually just left all the food and drink untouched and paid the bill.

Bartended for a decade. For a while, I was at a medium range Italian restaurant. More than once I saw a first date go awry because one of the two drank too much.

Most memorable was a woman who started downing punches. They were at a table so I couldn’t see them and I guess the waiter had forgotten his “red light, yellow light” training (I don’t know if they still do that). After the sixth one I asked if these were all going to the same person and he said yes. I was like, oh crap. Sure enough, girl ended up puking all over my bathroom and locking herself in. When we got the door open she was passed out and there was puke everywhere including all over her. No cab would touch her so the guy ended up taking her home.

He came in a week later and said they were going on another date. I was skeptical. They’ve been married for about 15 years and are absurdly happy. She avoids punch.

Happened at my former restaurant. Reservation for 6:00, young guy comes in a few minutes early, tells me he’s kind of nervous because it’s a first date and he hasn’t had many before, bla bla bla, kind of sweet really. Anyways, girl arrives about half-an-hour late, and proceeds to get very, very hammered.

About mid-way through the meal, she answers her phone, takes the call, and starts talking about her date, in front of her date, saying stuff like “well, he’s not usually my type, I don’t exactly like him, but I felt like why not”, right in front of him. Young man looks so discouraged, walks up to me, pays his bill, and leaves.

He’s a really nice guy, he’s come to the place I work at now a few times.

I work at a fairly nice Italian restaurant, where we do a lot of business. One night a man who I was not even serving came up to me while I was punching an order in on the computer and hands me $20 and a napkin with a phone number on it.

He proceeds to tell me, “I am on the worst date of my life, this woman is horrendous and I have to get out of here. Take this $20 and please go to the nearest phone and call me and tell me that I have to get home right away. I don’t care what excuse you make up, I just gotta get out of here.”

Initially I thought he was kidding until 2 minutes later the guy who was serving him came up to me to tell me how wicked this woman was and how he could tell the guy didn’t wanna be there. I promptly called that guy as soon as I had a free minute.

One of my shining achievements as a server.

There was this young guy eating dinner with his mom. I noticed they seemed weirdly uncomfortable and distant but didn’t think much of it. Turns out the lady was not his mom. He had met her on a dating site and had been VERY clearly catfished. The lady was at least a good 20 years older than him.

When she left the restaurant he stayed behind and told me about what happened then asked me out. I politely declined but agreed with him that that was a really weird situation.

I was a waiter as a first job.

It was an attractive young woman and an average-looking man. First off, these people were 30 and I have no clue why they decided to go to Applebee’s for dinner.

The guy was wearing plaid sleep pants and a over-sized red zip-up Columbia. The woman was dressed more nicely, but it was still casual. All goes well until it comes time for entrées. This guy orders a ton of ribs (a few full racks) and refuses the girl her original order of a house sirloin, which was only about $6, less than a fifth of his order. The man orders a $4 salad and a water for her. The woman stops talking completely while the man talks about some crazy party he went to. The man guzzles a few Strawberry Quencher Iced teas, says “See ya Friday, beeyotch!” and leaves her with the bill.

She said the guy seemed nice when they talked on Tinder, but was very uncomfortable with him in real life, and afraid to say something. A co-worker and I paid for her meal, and later she and the same co-worker starting dating, and they are engaged now.

Served a couple a few months ago. Every time I walked over, he would always be the one talking, and she would just be sitting there not having a good time. At the end I asked if it was one bill or separate and she immediately piped up “SEPARATE”. I go and take his payment, and as I hand over the Debit machine to the girl, I see the guy take his phone out and start swiping through Tinder.

A few years back I was working at Pizza Hut as a driver. We had the smallest store in the area, and there were no booths or tables for customers. You come in to pay and leave. There is one small bench barely able to seat two inside the door. This “couple,” probably freshman, come in and the lad nervously orders a single medium pizza. The whole time ordering it, he was trying to be very literate and use a bunch of old English sounding phrases to sound appealing or smart or something.

Fast forward the 10 minutes of cooking time he spent crammed on that tiny bench with the girl, who was visually uncomfortable, but also either too polite or too nervous to leave. I was hoping they’d leave and take it to a car or to the park but no. He started trying to hand feed her pizza. On a bench too small to comfortably seat two. With three to four customers in line less than two feet in front of them, and drivers constantly having to step over their legs to get out of the store.

In-between the cringy “want another bite?” offers, she was practically shaking at this point and closing her eyes out of embarrassment. That was a big mistake, because he slips in for a kiss instead of pizza. Regrettably, it worked and she threw up on the rest of the pizza in his lap. She bolts and runs off, he tries to order another pizza to go, because “she didn’t get to finish it, she’ll like it if I bring her another.”

I was working at a Mexican restaurant at the time. I was waiting on a couple and I could tell it was a first date by the questions I heard them asking each other. Anyway, towards the end of their meal there was this Hispanic girl sweeping next to their table and the woman looks at her, holds out the remains on her plate and says, “would you like to take this home to feed your kids?” I stood there in complete shock. This woman spoke no English, but she could tell this random woman was completely degrading her. The sad thing is she seemed like she really thought she was doing a good deed. Her date looked so embarrassed.

Olive Garden, around 2014 or so, from like 7:30 – close on a weeknight.

Middle-aged man of sub average attractiveness was sitting alone at a table with a glass of water, insisting that his date would be “just a few minutes, there’s traffic”. At around 9:15, manager had to come out and let him know that the restaurant would close at 10, and if he’d like to place a food order, he should probably do it now. He ordered a bruschetta appetizer, and said again that his date was on her way and they’d order when she got there.

9:45, this BEAUTIFUL woman walks in and awkwardly stands by his table. I couldn’t hear the conversation they had, but the man then asked for a box for the appetizer and they wound up leaving together without her even sitting down.

Once witnessed a date where the dude talked about how special he was and how his mind wasn’t like other people’s for the entire date. The girl was politely nodding along and every time she tried to get a word in, he’d cut her off. Absolutely brutal.

I’m a waitress at a mid-range priced bar/grill. Just yesterday, a younger couple came in, and as I greet them I ask if they want anything besides water. Conversation is as follows.

Girl: May I have a Coke? Or Pepsi?

Boy: God, Erin. I’m paying.

Girl: Water will be fine actually.

My heart immediately sank, because you bet your butt he tipped less than 10% too.

I work at a pretty high end steak house. I sat  a table of two and when I greeted them, assuming they were a couple. It took them quite a while to order their food — I had to go back quite a few times and ask if they were ready. After an hour of them talking, ordering cocktails, and looking at the menu, they finally ordered. The woman ordered a filet mignon and the guy ordered our most expensive steak.

Right before their food came out, I saw the guy get up and walk towards the bathroom. My coworkers ran their food to their table and the woman sat there with all the food in front of her. I thought he was coming back soon, but around 20 minutes went by and there was no sign of him.

My manager walked over to me and asked me what was up with them. I said the guy was in the bathroom. My manager went and asked her if she wanted us to keep the food under the warmer. She said yes, and the food was under the warmer for maybe an hour while she sat at the table alone.

I walked over to her, and asked if everything was alright. She immediately broke down, said it was their first date and that they met on Tinder. Apparently she told him that a steakhouse was a little much for a first date and suggested coffee instead, but he said no. As they were sitting there talking, he looked at his phone and said “my daughter has an emergency” and he quickly got up and left. She was texting him after and he never replied. This girl bawled to me for 20 minutes, repeatedly saying “what’s wrong with me?” I had to reassure her he doesn’t know what he’s missing blah blah.

I went over to my manager and asked what we should do about the check. He said he was stuck, because it was a $250 tab and that’s too much to just not have her pay. After a few minutes of convincing him, I got him to take everything off the bill. I boxed up all the food (including his steak and sides), brought it over to her and told her to enjoy her night. She stopped crying, thanked me, and left.

I witnessed a couple on their first date having a few drinks. They started making out by the third. Dude was crying by the fourth. He started sucking on her finger. Then he cried again and abruptly ran out of the bar and down the street. She paid.

Then this dude came back to the restaurant two weeks later. I pretended not to recognize him to be nice, but he brought it up! “I think you served me on a date two weeks ago.” “Uh, I dunno man I serve a lot of people.” “Yeah, it was you, remember? I cried and ran away?” Dude, why are you doing this?

Worst one I ever saw… two people who were probably perfect for each other; they were both completely self absorbed. How completely? They both started stories and kept telling them at the same time. They weren’t even listening, just talking at each other. I was so enraptured by the sheer insanity of it that I didn’t do anything for like 45 minutes as they both just yapped away, barely stopping to breathe.

Waiting tables at a fairly high-end place. My recently divorced brother’s ex-wife came in with her new “rich lawyer” boyfriend – she knew I worked there.

Lawyer-boy’s credit card was declined and she had to pick up the tab.

When I was in high school, my college-aged sister took me to a concert. While we were waiting for the show to start, we noticed a guy and girl in front of us who were clearly on a first date. Their conversation was so awkward that it literally devolved into talking about the weather. Brutal.

Because we’re terrible people, my sister and I decided to make fun of the couple by mimicking their embarrassing conversation. After a few minutes of our antics, the guy half-turned his head toward us with a look of pure desperation on his face, as if to say, “For the love of god, please don’t make this nightmare worse than it already is. I’m begging you.”

We stopped. A few weeks later, my sister came home from a party and told me, “Remember that guy we made fun of at the concert? I just met him. We’re going out on a date!” They are now married with 4 children.

I work at a country club that is up to its ears in old money that uses said old money to make more new money –the membership fees cost more than a year at my university. To say money is not an issue there would be an understatement.

Anyways, I was serving a young couple and the power imbalance was phenomenal. She was the daughter of one of the board members and the entire staff knew her (read: her father’s) club account was major money. And the gent, well he wasn’t a member, and certainly looked like he was just the average broke college student. He was wearing plain but nice clothes and she was dressed to the nines in fashion.

The date seemed to go smoothly enough, nothing out of the ordinary. Until she gets up and leaves the table before I have brought out the bill. I bring the bill to the counter (knowing it is well over $300 worth of food and drinks, all things SHE insisted on ordering –2 bottles of top shelf wine, neither finished–two steaks, when he asked for the chicken and she insisted on him eating steak “like a man”).

He solemnly goes to pull out his wallet and starts tearing up, apologizing that he won’t be able to tip. I mean, I’ve never had a customer cry over not being able to tip. And he further explained he was a server too and that she didn’t know he wasn’t rich and she left because he had told her about his scholarship.

I was flabbergasted. And kindly reminded him that at this country club we do not take credit cards nor cash, we only charge to accounts. And so her father got a hefty bill. It was entirely satisfying.

Last I heard, her father cut her off. I can’t help but smile at all the life lessons she is learning — like working to go on dates.

I own a bakery, I see a lot of awful first coffee dates and awful people in general, but there’s one that will always be the worst for me.

This happened at my bakery maybe six months into our first year. Two boys come in, chatting normally, clearly on their first date. They’re both young, maybe 15 at most, and adorably nervous. They order at the counter and go find a table, sitting close. One of them starts holding the other’s hand, playing with his fingers, just being cute.

All of a sudden this woman comes up and starts berating one of the boys. It was his mother. She had shown up because she wanted to meet the girl because her son was being cagey about who it was (I assume he had mentioned where they were going because she wouldn’t let him out if she didn’t know). She starts screaming and crying about how her son could do this to their family. Doesn’t he know she wants grandkids? His father would be so ashamed if he was still alive, doesn’t his father’s memory mean anything?

She then tells him that if he keeps up with this, don’t bother coming home, and then marches out of our shop. This poor boy is just weeping, while his not-even-really boyfriend is trying to comfort him, completely bewildered with what happened.

He made a comment to her about how he’s “not Jewish” so he’s not cheap and she should order whatever she wanted. She was Jewish. Spent the rest of the evening in silence as he went on about how his ex girlfriend was anorexic and “so annoying about food.” He was happy to be on a date with a woman who could eat like a normal person.

So weird.

Worked at Applebees. This woman was the worst woman I’ve ever waited on. She was needy and slurped down her iced tea like there was a world wide shortage. He was silent. He didn’t talk once except to order his quesadilla burger, and she just kept going and going prattling on. And she was mean too! Talking down about how people were losers to be servers, and how much better it was to work in a shop.

At the end, he went to the bathroom and just never came back. He apparently jetted out the side door where the to-go girls worked and gave them a twenty to give to me. Worst Woman was just sitting there and waiting for him to come back. I stood there at the servers station just waiting for her to realize he wasn’t coming back.

So after ten minutes, she just started crying, pushes her chair over, and flounced out. I didn’t get a tip, but it made my night.

I once saw a guy try and impress his date by pretending to know about wine.

He then proceeded to pronounce every single wrong one. I don’t even know how I would phonetically write out his butchering of Chablis and Sauvignon Blanc. Date looked at him like he’d just taken a dump on the table.

I worked for IHOP for a very long 3 months. Most of my experiences were decent.

On one occasion, one of my acquaintances came in with a date. We had been friends as kids and still sometimes chatted amicably. At this time, I had a stutter that would happen if I spoke too quickly, was stressed, or just trying to speak hard words. I went up to their table, said hi to my friend and her date, and instantly flubbed the greeting with a stutter. Honestly, my stutter has never bothered me, never felt like a bad thing until that moment.

Her date look at me, did that little condescending laugh that we’ve all heard before, and then repeated what I said while mocking my stutter. I could see my friend physically recoil from him, her face clearing showing a ‘did you really just act that way?’ expression.

At the time… I just brushed it off. It bothered me for about two seconds in the moment, but even years later I still haven’t forgotten.

Still, I could tell with that one little moment of jerkishness, my friend was not gonna go on a second date with him.

Man and woman cozy in a booth. Different woman storms in through the front door literally dragging two kids behind her, right past the hostess station to stand defiantly in front of the couple and proceeds to ream out the man, who is clearly her husband. Dude was humiliated, but those poor kids, though.

Girl and guy came into the barbecue restaurant I worked at. They met at the door exchanging the usual “Hi, nice to meet you!”, etc. The guy was a complete weasel. She ordered ribs and he said, “Do you want to keep that hot figure of yours or look like that chick over there? ” He pointed to a slightly overweight woman. Then, when they were waiting to pay (before getting their food) he started flirting with the chick behind them. She waited until he paid then left without even waiting for her food.

Couple in their mid-twenties come in, it’s obviously a first date but they seem to really like each other and are getting along well. I wasn’t serving them however, I was serving the table next to them.

About halfway through their meal I notice them holding hands over the table. Cute. Then, the guy lifts her hand to his lips and kisses the back of it. A bit of an outdated gesture, but still cute I guess. The woman seems slightly confused but goes along with it.

A little while later I see the guy do it again. Okay, dude. Then again. Woman is confused and looks a little uncomfortable. They are no longer holding hands. I go to serve my table and see the dude full on MAKING OUT with her hand, tongue and all. Woman looks extremely embarrassed and uncomfortable, looking everywhere but at her date.

I go over and casually ask if they need anything, and the dude stops. Woman yanks her hand back. She left pretty soon after.

I was working in a small restaurant with two floors. A woman and a man came in and I had a table for them upstairs. It looked like they were on a first date because they were asking those “getting to know each other” questions.

After ordering food, the woman had to go to the toilet, which is downstairs. As she walked to the stairs, the food arrived. She walked down, tripped and fell all the way down knocking her head on the ground. Two colleagues immediately rushed over to her to see how she was doing. She was unconscious and bleeding from her head so they called an ambulance.

I went to the man while he already started eating and told him his partner (didn’t know what else to call her) fell down the stairs, that she was unconscious and that an ambulance was on the way. He walked to the stairs, looked down, and walked back to his table to finish his food.

Later the ambulance arrived and I asked him if he wanted to go with them to the hospital and he said no while finishing her food as well. It was so awkward he just sat there for another 45 minutes eating, drinking, paid the bill, and left. I still don’t know what kind of relationship they had and whether the woman was okay.

Girl was obviously super into guy, and he seemed like he was at least somewhat interested. They both talked and joked with me, overall great table. Cut to the check, I ask if it will be together, and the girl smiles at the guy. He promptly says, “No, separate please.” Her face dropped, and he blatantly wrote his number on the check with a little note for me. That poor girl almost cried as she quietly shuffled out the door. What an idiot he was.

I cannot miss the opportunity to share this story:

Friend and I meet up and a chain restaurant for a meal and a catch up. In the booth across from us are a guy and a girl in their twenties, very obviously on a date. Things seem to be going moderately well, just kind of let them do their thing in the background as my friend and I chat about life and stuff.

Then…

THEN…

Guy stands up halfway through the girls sentence, cutting her off. It’s quite a violent standing so draws the attention of most tables nearby. Guy then says this in a way that makes me think he has rehearsed:

“I’m sorry, Jen. I just wanted to give women one more chance but I can’t do it, your lively but women just aren’t doing it for me.”

Guy throws some money on the table and walks out. Jen kinda sits there with everyone looking at her, going redder and redder. Lovely waitress swoops in and saves the day for her, but wow.

Never seen anything that completely insane before or since. At least just wait for the date to be over and politely decline a second.

Not as good as some of the other ones here but I definitely have a memorable one.

Was waiting on this couple, who are clearly on a first date. The man seems initially delighted with her. I take their order and she orders the Fettuccine Alfredo. Cool no problem.

I bring their orders out and as is custom at our restaurant I ask the lady if she would like some fresh grated Parmesan on her pasta. She goes “oh yeah. I looooove cheese. Your arm is going to get tired I’m warning you!” Her date smiles at her, clearly thinking she’s adorable.

Now I’ve heard this and dealt with this before. I have grated a lot of cheese in my serving career. It’s never been a problem and I almost never judge someones cheese preference, being a dairy lover myself.

I will never forget this lady. I have never grated that much cheese before or since. It starts off normal and her date is still smiling at her. The pile begins to grow and he chuckles, clearly thinking this is some cute quirk.

But she doesn’t tell me to stop. You can no longer see any pasta on this dish and our dinner pasta portions are very very large. I can see on his face that his initial delight with her is slowly morphing into surprise. The smile is growing smaller and tighter and the eyebrows are going higher.

And still she doesn’t tell me to stop. She’s clearly thrilled and obviously wants MORE cheese grated on this thing. For the first time my arms and wrists start to hurt. Now there is no where left for the cheese to go but UP. A small humped mountain of parmesan is growing on this womans plate. FINALLY after what seems an eternity she says “OK! That looks great!”

I am not exaggerating when I say she was having some pasta with her cheese. I had to get a fresh block because it was worn to the nub. My wrists hurt like hell. A first for cheese grating in 8 years. This dish looks absolutely gross. I look over at the guy’s face and it has now morphed again from surprise to pure disgust and embarrassment.

She is completely oblivious and digs into her cheese stack still chirping and chattering at him and he won’t even make eye contact anymore. The smile is gone. He is clearly over it. It’s very obvious there is not going to be a second date.

I skip asking if they want desert and bring him the bill as quickly as I can without appearing to rush them. He gives me a look that all but screams “Thank You!” and makes his excuses to go, leaving me a VERY nice tip for expediting this painful experience as much as was professionally possible.

Haven’t seen either of them back since.

I worked as a waitress in an Italian restaurant while in uni in 2006. Obvious first date comes in. He’s booked it and requested a table in a secluded area of the restaurant because the acoustics would be perfect.

She arrives and asks to move table to by the window. No big deal. He’s annoyed at this. They ordered a carafe of the house red with their meals. Anything she said he’d turn it into some achievement he’d already accomplished. He kept making comments about her order, such as how fattening a dish would be,and then proceeded to say his family owned a vineyard and he knew a good red wine when he smelt one.

He then asked for the most expensive wine on the menu and to take away the what he called “trashy house wine” then talked about how the bouquet was different and the clarity was so much better on the “expensive” wine.

When it came to dessert she had had enough of his idiocy and flipped when he said that she shouldn’t have any or she’d end up with stretch marks. She was a bit overweight but not overly so. She stood up and yelled at him for being a condescending piece of crap, for knowing nothing about wine and dropped the coup de grâce that her father was our wine supplier and that the house red was exactly the same as the most expensive wine (all of which was totally true).

He was left speechless with the full check to pay.

Couple years ago, I was tending bar at a high-end steak joint. A pretty brunette walked in and sat down at the bar. After fixing her a cocktail, I asked if she’d like to see a dinner menu. She explained that she was waiting for a date.

A few moments later, the guy arrived carrying a large bag.

It was immediately obvious this date was their first. Their conversation was lurching from forced to downright painful when he reached into the bag and pulled out an album containing…

…his Pokemon card collection.

He set the book on the bar and thumbed through each page, thoroughly and lovingly describing every card, attempting to educate his date in the ways of Japanese pocket monsters. I’ll be fair to the guy – dude was passionate.

She feigned an emergency and called her friend to pick her up. He stayed and ate a plain hamburger at the bar.

Both of these people were in their mid-30s.

I once had a guy come sit at my bar who was waiting for his blind date. He orders a couple of drinks to calm his nerves. Well, he probably should have slowed it down to keep his mouth from working faster than his brain… Anywho…She shows up and is waaaaaay out of his league. She is absolutely beautiful. She orders a drink and they start talking. I come back to check on them and I hear him talking about how much he hates children. He was saying things like how he hopes he never has any, and that he will never be stuck taking care of them, and how he wishes that kids couldn’t be taken into public places so that he wouldn’t have to be around them.

She looked him dead in the eye and said, “Well I have a daughter, and I love her very much.” She grabbed her purse and walked out on him. …The look on his face was absolutely priceless.

This was about 15 years ago. I was a trendy restaurant late at night with a friend and besides us we had a couple that was on their first date. The girl was hot and had a very alluring voice which captivated me. I kept staring, that voice…

At some point you could tell she was not interested; twice she took calls and left the table. You could also tell the guy had figured it out so he asks for the bill, girl was still on the phone (later I found out with a friend begging for a ride). So dude pays for the bill and vanishes.

On our way out, the girl was still waiting for a friend, I started chit chatting with her and man did we connect. We mostly bonded  by talking about how cringy that date was. She almost peed herself, we laughed for like an hour.

So she eventually decided to tag along with my friend and I. We met up with friends at a nearby night club and we ended up dating for like 3 years.