Epic First Dates That Will Give You Worst Impression About Dating

We have all imagined how our first dates would turn out. We thought it would be magical and romantic. We thought it would lead us to a real-life fairytale. No one said that it could be messy, cringy, and traumatizing.

Well, brace yourselves because what we have is an actual compilation of nightmare stories that came from our Redditors’ first dates. These will make you think twice about dating. Come check these out! 

1. Dating Bump

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 had 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. She walked to the stairs, and the food arrived. She walked down, tripped, and fell 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 had fallen 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 her 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.


2. The Breakup Connoisseur

I have seen a lot of awkward last dates! I used to work at a very small neighborhood restaurant. Everyone that came in was a regular. Most were couples in their 40 to 50 years old. They were mostly out for a quiet dinner, but there was one stand-out.

A very handsome man in his early 30s would come in only to break up with women. About twice a month he would come in with a beautiful woman and partway through their meal she would be crying. I always tried to clean the tables near them for as long as possible but I never heard much of his speech.  

He always tipped well and was super nice to me and my coworkers. It was just brutal seeing him bring in a new lady and knowing what she was about to go through.


3. Date Feast with a Side of Silence

I work in an Italian restaurant. A few years ago I waited on a guy and girl who met for the first time upon arriving at the restaurant. There were awkward pleasantries exchanged at the door and then they were seated.

When I was taking their order the guy asked if we had soup because he had mouth surgery a few days prior and chewing food was still a little rough. We don't have soup, so I explained that the "softest" food on the menu was gnocchi.

He ordered the house gnocchi and proceeded to cut each tiny dumpling into four or more pieces and slowly chew each piece. He ate that entire dish over 3 hours and the girl stuck it out for the whole thing. She looked miserable and I'm pretty sure they never saw each other again.


4. Mystery Of The Missing Date

I worked at a cafe and it was a small local chain so there were two other locations in the city. This guy sits down for about an hour and comes up to the counter and asks if we can call around to the other locations to see if this girl was there because they had a date planned and he was sure she must have just gone to the wrong location.

We called the other two locations and they said they never saw anyone fitting that description. The guy stuck around for another couple hours, buying two more drinks and a sandwich just waiting until we finally closed for the night. I felt so awful for him! He seemed so crushed.


5. Awkward Appetites

On the first date that I witnessed, he commented to her about how he's "not jew-y" so she should order whatever she wanted. She was Jewish.

They 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. One of the only times she spoke was to respond that she was Jewish. It was a quiet night in my restaurant and I was nearby doing sidework. She seemed like a very shy person.


6. First Date Fire Escape

I was bartending in New York and watched this couple that had met on a dating app have their first date sitting at my bar. The girl was a complete maniac.

She kept bringing up the fact that the dude she was with could be a psychopath and could end her (he had not indicated this) and went on a dating app while he was still sitting beside her at the bar.

She kept telling him he was lucky that she agreed to meet him at all and she didn't think he'd be this boring. She ordered about 5 or 6 LITs and several shots, he literally just had 2 beers. She made him pay for everything.

My favorite part of this show was that he excused himself to go to the bathroom and left through the fire escape. Absolutely brilliant. To be clear, there was only one official entrance and exit. This dude escaped out the back and she went searching for him. She straight-up thought he had disappeared out of the bar.


7. Fleeting Date Night

A 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, the 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. At 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.


8. Lost In Good Intentions

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, this Hispanic girl was sweeping next to their table and the woman looked at her, held out the remains on her plate, and said, "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.


9. A Weekly Odyssey

I used to work at a little diner place, definitely not the type of place to bring a first date. There was this guy who'd come in every Friday with a different girl. He was a very good-looking dude and was always super polite and very nice to me, but he was super awkward.

The girls would look kind of skeptical as they walked in (probably because of the crappy diner scene). 

Every week, about halfway through the meal, like clockwork, the girls would develop these "get me the heck outta here faces." That's when I would bring the check. They always boxed up their food and left right away.  

I had the chance to talk to one of them while he was in the restroom. Apparently, he wasn't harmful, there was just something off about him that the girls didn't like. His persistence is on point though.


10. Ego Overload

I once witnessed a horrible date that was so painful to watch. The dude was so full of himself that he couldn’t seem to notice the girl he was dating. He just 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. The poor girl couldn’t even talk because every time she tried to get a word in, he'd cut her off. It was like he was the only one on the date. Absolutely the most brutal date I have ever seen.


11. Stood Up To Showdown

A guy got stood up. He then drank a magnum bottle of red wine (8 glasses of wine) and ate 3 apps out of desperation. His date called him and he started cussing her out. He asked for more wine and then I had to cut him off.

So, he got up and tried to run out of the restaurant with a bottle he grabbed from a rack. An off-duty cop tackled him in the lobby and then he craps on his pants in front of everyone waiting for a table.

He lay there screaming with the guy holding him down until the cops arrived and arrested him. This is my fondest memory of being a bartender at a restaurant.


12. Riches Clash With Reality

I work at a country club that is up to its ears in old money and uses said old money to make more new money. 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.

The gentleman 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 got up and left the table before I brought out the bill. I bring the bill to the counter. it is well over $300 worth of food and drinks, all things she insisted on ordering. Two bottles of top-shelf wine, neither finished, and two steaks. When he asked for the chicken 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.

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. I kindly reminded him that at this country club, we do not take credit cards or cash, we only charge to accounts. So her father got a hefty bill and rest assured he signed a handsome tip to me in her name. 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.


13. The Silent Escape

I worked at a restaurant. This woman was the worst woman I've ever waited on. She was needy and slurped down her iced tea like there was a worldwide 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.

In the end, he went to the bathroom and just never came back. He jetted out the side door where the to-go girls worked and gave them a twenty to give to me. The worst woman was just sitting there and waiting for him to come back.

I stood there at the server station just waiting for her to realize he wasn't coming back. So after ten minutes, she just started crying, pushed her chair over, and flounced out. I didn't get a tip, but it made my night.


14. Good Intentions Go Awry

This is a story where the guy was doing pretty good until my boss messed it up for him. So there was this couple on a first date, seated at a table in the back. At first, I didn't think much of it and wasn't even aware that it was a first date until the restaurant's phone rang.

A man called to let me know his son was there on his very first date ever (the son was in his late twenties). This was a big deal to him and he called the restaurant to make sure we would do our best to make sure they have a pleasant evening.

My boss heard and instantly went to the kitchen to make sure they would get “special treatment.” What followed was plates with rose petals and red hearts. Way over the top. When serving the plates my boss even mentioned the phone call. To finish it off the desert came complete with fireworks and all that.

The idea was sweet, but obviously, this was way too much for a first date of two people who were just getting to know each other. As the evening progressed the girl was visually put off by my boss trying too hard. Poor guy. Up until then, he had been doing quite well.

The pair seemed to have a lovely evening. Until my try-hard boss entered the scene that is. The girl was polite towards the end of their date, but it was obvious there was not going to be a second date. And it wasn't even the guy's fault, other people ruined it for him. I felt so sorry for that dude...


15. Foot In Mouth Fiasco

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. She shows up and is way 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, 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.


16. Emergency Escape

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 handed 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 makeup, I just gotta get the hell 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.


17. Navigating Awkward Realities

It was one of my first dates where the waiter definitely could sense the awkwardness. I was a junior in high school. I had been flirting with a senior for a couple of months and asked her out the day I got my license.

I picked her up from her house and within 1 minute of being in the car, she got a phone call. One of her best friends passed away from a Brain Aneurysm earlier that day.

I told her that we could delay the date and offered to take her home, but she declined and insisted we carry on. We get to the restaurant and she is crying at the table. I didn't say any words to her other than "Are you okay?" the whole date because she was either texting her group of friends or couldn't make out words due to being so hysterical.

The waiter kept coming by and sensed how awkward I was feeling. Out of all my restaurant experiences, I have never received my entrée and check so fast. The waiter was a true bro.


18. Barroom Drama

My bar has two floors, and on this night I was working upstairs. The couple came up with beers they already had bought and sat in my section. I go to introduce myself, the girl seems nice, but the guy says nothing, and just stares at his beer.

They eventually get another round, and as I'm dropping off their drinks, I hear the guy slur out in garbled words "Thank you very much." He's wasted. It was just a beer anyway, nothing too strong, but it will be his last round.

I go about my business for a while. At one point I glance up at their table. The girl is gone, and the guy looks horrible. I thought to myself "He looks like he's about to puke" and right then, he hurls.

Not a lot came out, and he tried to pass it off as a cough, but I saw enough pour out of his mouth, onto his chair and the floor.

I grab my barback and a trashcan. Barback gets to work on the vomit and I put the trash in front of the guy. I told him to go to the bathroom, take the can with you on your way, then get out. He says nothing, just stares at his phone for a minute, then gets up and leaves.

I race around looking for his date. I found her at the bar trying to pay her tab. I tapped her on her shoulder and tried to tell her about her date, but when she turned around, her face told me everything.

The shame and embarrassment that glazed over her might make one think she was the one who just tossed her cookies. That's when she told me it was their first date.

They had met through a mutual friend, and she didn't know him at all. My bartender and one of our awesome regulars overheard. We paid her tab. She ended up staying at the bar hanging out for a while as the aforementioned regular bought her more drinks. Real nice lady.


19. Going Beyond Chivalry

I have seen everything from crying to ketchup ramekins being thrown. The only obvious first date I ever noticed is as follows. Above average-looking guy sits down and says he is waiting on his blind date to show up and I tell him I'll keep my fingers crossed.

The girl shows up a half hour late and she is not attractive. She was probably 120 pounds heavier than what he was looking for and her face. I got an "Oh well" look from the guy when she was in the bathroom. He didn't say anything to me. Just had his dinner.

Every time I refilled the glasses, there was a conversation with both people smiling. At the end of the meal, he paid the whole tab and tipped well. After they said their goodbye I caught up with the guy.

I had finished all my tables and wanted to know if he was seriously okay with being set up with someone so obviously not in his dating demographic.

So I asked how his meal and date were. Then ask if there would be a second date. He laughed and said not likely. I told him that's what I thought but they seemed to be having a good time.

He told me, "That girl probably hasn't been on 3 dates where the guy paid and was genuinely nice. Why wouldn't I be a gentleman? My friends are douches, but she did nothing wrong and deserves to be treated like a beauty now and then."


20. A Double Date Disaster with Captain Mal

My best friend and I got tickets to an advanced screening of Serenity. Nathan Fillion was in the audience and conducted a panel discussion after the movie.

He wanted to ask out this girl and she agreed if she could bring a friend and we could double date.

My date and his date had never heard of Serenity or Firefly and hated sci-fi. Her friend insisted on the following seating: Me, My friend, her, and my friend's date. so no one was even sitting next to their "date."

The movie ends and Nathan gets up and asks who in the theater did not cry when someone passed away. Our two dates were the only people who raised their hands in the entire theater. He pointed to both and called out "Robots!"

Our dates were called out as unfeeling soulless constructs by Captain Malcolm Reynolds himself. They did not talk to us on the way home as we dropped them off.

It was simultaneously the most awesome and worst date I ever experienced.


21. Mama’s Boy Meltdown

There was this young teenager who brought his girl on a date. They are young enough that they need his mom to bring them. I thought the mom would just drop them off and leave. But the boy is overly clingy and acts like a kid.

His mom is cool and offers to go sit at the bar so they can have privacy. He tells her no and insists that she should stay with them. He then proceeds to talk only to his mom the whole time they were there.


22. The Whistleblower's Sacrifice for Love

I have been a bartender and a waiter over the years. This good-looking dude was sitting at the bar and had a date with this girl that his best friend liked. His friend just refused to ask her out because she was into him instead.

He was getting into his story when she walked in and he clams up like someone shocked him. She was by anyone's standards drop gorgeous and killing it in a little black dress and high heels.

She comes up and she orders a tequila shot with a lime. He does one with her and they banter about getting that out of the way and move into a little more intense banter. He whistles at me again like I am a dog. "More shots!"

Disappointed, I go to pour him a shot and let him know I am not a dog. I retire to the sidebar real quick and one of the other guys starts to talk to him while the girl goes to the ladies' room.

When she gets back he whistles at the other bartender again, "Hey man! Where are my shots? Pronto!" This guy starts just hammering shots. The girl only did one and is sitting there sipping a wine.

The dude starts to get a bit sideways. Laughing at his jokes and talking over the girl every chance he gets. He then announces that he has to piss on a rock. The girl looks mortified. She is texting away like a madman. He starts talking to different girls at the bar.

He is not piss drunk. His friend follows quickly after and the girl is left at the bar alone. Five minutes later the friend walks in, sits down, and has a drink with the girl. I heard him say that he put him in an Uber and sent him home.

About 30 minutes late, the boy walks back in sober as the day he was born! Sits down waves me over and apologizes for whistling at me. Give us 20 bucks and buy us a shift drink for when we get off.

He did it all for his friend. Got 1/2 drunk played the fools and called him to come save the day. Honestly said, "he is a better man for her than me. She is just not my type". I was stuck between awe and impressed.


23. Date Night Dilemma

I worked at a popular chain restaurant and served a couple that had met that day at the grocery store. He picked her up for the date. I offered them to try our drink specials, but she said she was on some "loony" pills that she couldn't drink alcohol.

Meanwhile, the man ordered a Long Island. She told him, that it was unfair for him to be drinking in front of her when she couldn't. He disregarded this and was ordering drinks.

While they were waiting for their food she went to the bathroom. Their food came out and she was nowhere to be found. Eventually, after the man was almost finished his food he asked me to check on her in the bathroom to see if she was alright.

I found her standing in the mirror and told her that her date was wondering about her. She then went on a rant to me about how it was unfair of him to be drinking without her and how he "doesn't want to see her off her pills" and how she "can't be with a man that will do that to her" but he gave her a ride there so she couldn't leave without him.

I suggested she take an Uber home she informed me that she didn't have her wallet with her so she was stuck. She told me to tell her date that she just had her period bad and didn't have a tampon. I told him what she told me to and at that point, he had finished his meal and just patiently waiting for her.

She eventually came out and started arguing with him over his "drinking problem" and started to get defensive and mad about her "ditching" him in the bathroom. After making a huge scene he stormed off and left her there. So now this crazy woman was stranded at the restaurant with no wallet at midnight.

She started wandering around the restaurant asking every table for money, asking every server for a ride home, and following people to their cars on the way out of the restaurant wanting a ride. My manager eventually kicked her out for soliciting and then called the police because she was trying to get into employees' cars with them


24. A Muffin Of Fate

We had a girl come into the bakery where I work to meet someone from a dating app. This girl was cute and I had been crushing on her for a long time, so I was getting pretty antsy about watching her go on a date at my place of work.

Anyways, about 20 minutes into her sipping her coffee, her date walks in the door, takes one look at her, turns around, and leaves. She's starting to tear up while she dejectedly takes bites of her muffin and I am trying to peel away from the rush of customers to go console her for a second while wiping down tables.  

Before I get the chance, a guy who also saw the whole thing sits down with her and they get to talking and eventually leave together. That was two years ago, they're getting married now.


25. Unlucky Valentine’s Day

Well, I'm not a server, but my personal worst first date involves a bartender and a waitress, so close enough? Anyway, this bar that used to be in my hometown did $4 pitchers of domestic beer, 50-cent hot wings, and free pool on Thursdays, so me and my buddies would go every week. That's where I met her.

So eventually I asked her out, and she said she'd like to go out sometime, but she was seeing a couple of other guys, too. Fresh out of a relationship and all. But pretty much every time I tried to take her out she was busy.

So February 12th rolls around, and she hits me up. The other dudes she's talking to all have plans for Valentine's Day, nobody asked her to do anything, etc. So I hit up a friend who works at a restaurant, he gets me in after somebody canceled, and we're good to go.

Go out to dinner, have a good time. On the way home, she wants to stop for a couple of drinks. Sure, no big deal, right? So we have a couple of beers, shoot a couple of games of pool, and she goes outside to smoke.

I clear the table, rack the next game, and go to the bathroom, and our waitress comes back around and tells me she's hooking up with the bartender in his car. So I go outside and sure enough, she's screaming away in the parking lot.

Long story short, the waitress was covering the bar, so I ordered a shot of whiskey, and she gave me some single-barrel bourbon on her. I drank about six more, told her that my date was paying the tab, and left the chick there.

About an hour and a half later she called me to ask where I was. She didn't have the money to cover the tab, the bartender wouldn't give her a ride home. I found out eventually that she had to call her dad to come pay the tab and pick her up.


26. Dining Disaster Turn Around

I was a waiter at my 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 this restaurant bar for dinner.

The guy was wearing plaid sleep pants and an oversized 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 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 four-dollar salad and 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 "Seeya Friday, wench" and leaves her with the bill.

She said the guy seemed nice when they talked on a dating app, 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 started dating, and they are engaged now. Not as interesting as everyone else's for sure, but I thought I'd share


27. Awkward Symphony Of Water

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. I offered them the menu for them to order.

They were talking about what to order and she said, “May I have a soda?" He replied a bit annoyed, “God, Erin. I'm paying.” The girl responded, “Water will be fine actually.” My heart immediately sank, because you bet your ass he tipped less than 10% too.


28. Blind Date Dine And Dash

My brother’s girlfriend set me on a blind date with her friend who is, in her words, "totally into heavy guys." So I go to pick her up and my alarms go off.

While she's not a 9/10 she is definitely what most would consider out of my league. I try to talk to her on the ride, at most I get noncommittal grunts of words in response.

We get to the place to eat, a steakhouse that's noted in my area for being nice but not super expensive, and get our table. We order our food. While waiting, I try to talk to her. Simple things.

She is from around here and has no hobbies. She just taps on her phone and gives me small two-word answers for the most part.

Food shows up, she picks up her plate and heads to a whole other table. Tells me her friends showed up and I was not invited. 

Meanwhile, she's sitting at this other table with a good bit of expensive food. I blink for a bit, I then call the waiter over and explain to him what's up. I want separate checks. He agrees. I go ahead and pay for my food.

She begins ordering drinks. Not just for her, but all of her friends. I just finish what I can with my food. About an hour later she comes back over and says she's ready to go. I wave the waiter down and tell him she's ready to go.

He brings her a check for well over $100. She just smiles and looks at me and pushes it towards me explaining I was paying. I push it back and tell her I'm not. Get up, and smile at her. "I've had a lovely time tonight. I hope you have good luck in paying your tab and finding a ride home that doesn't involve a police cruiser."

My brother's girlfriend began blowing my phone up an hour later about how could I do that to her friend. I shut her down fast. So whoever that waiter was, you're the man. Keep the $20 tip.


29. Mockery To Matrimony

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 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.


30. Heartbreak At First Date

I own a bakery, and 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. 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.


31. Awkward To Absurd

Not a waiter but my friend had a date that was so bad her waiter comped the meal. The girl and guy on a date, guy are awkward borderline weirdo, no chemistry, my friend would try to joke with him and he would look at her dead-faced.

So all of a sudden two wicked drunk women come over to the table and start saying like "You're too good for him girl," "Come home with us this guy sucks," and "You need to dump him" And they start spraying him with silly string.

He's covered, they run out, he starts crying and then leaves, and she is just sitting there stunned. The manager and waiter covered her bill and she has a great story now


32. Coffee Shop Casanova

  My friend has a favorite coffee shop that she frequents, and every time she goes, the same guy is there with a different woman. Every time, my friend overhears the man saying the same things: "Wow, you're gorgeous. You're the most gorgeous woman I've ever met," "I've never met someone like you. Never. You're special," and "You're totally different from any woman I've ever known. You mean so much to me."  

By the end, the woman always looks either embarrassed, bored, or completely frustrated out of her mind. And the guy always looks so disappointed and confused about where he went wrong by saying the same cheesy things to every single woman he dates. It's pretty sad.


33. Wheelchair Fiasco

It was my first date ever, we were both 15 and since she wasn't out to her homophobic parents, I was just a "friend" so we started the night with me lying to her mom.

We went to this relatively nice place that has everything. Pizza, salads, fish, you know? Pretty even mix of families, dates, and old people. We wait like 20 minutes for a table, and sit down, all normal. I should also mention I'm in a wheelchair.

So the waiter comes by and is just taking too long staring at us, trying to figure it out. I'm used to this crap, but I can tell how uncomfortable my date is. So finally the waiter pours our waters and gives my date a menu. She doesn't give me one.

Two minutes later she's back with a braille menu. I'm laughing my ass off, a sincere but nervous laugh. My poor date is sitting there looking mortified. At the moment I think that she probably just has no experience with this kind of ignorance. That's okay, I'll teach her.

Boy was I wrong. I say to her "It's okay, really" to lighten the mood. She looks me dead in the eyes and says "I had no idea wheelchair users were illiterate." In my 15-year-old social obliviousness, I thought she was joking, so I laughed harder.

She looked so sad and broken and I realized she was dead serious. I stayed because I didn't have a ride home. It was by far the worst dinner of my life.


34. Burger Bonding

Not a waiter but I remember when I was 10, I was at a restaurant bar with my dad and we saw this couple who were clearly on a first date.

They were holding hands across the table and when their food came they squirted ketchup on each other's burger still while awkwardly holding hands.

It looked like they both were having a good time so it probably wasn't a bad date, just awkward as hell to watch. From the looks of it, that dude probably got laid that night.


35. The Lost Connection

Back in like 2006 a guy who would now be considered a "hipster" came in. He had a phone hooked up to a rotary telephone (this was handmade, this was way before you could buy them). He was looking excited waiting for his date, half an hour passed, and he was looking concerned.

Then, someone calls him, and the saddest look ever came across his face. Halfway through the conversation on the phone, he unhooked the rotary phone.  

The guy left staring at the ground. I always hoped that he was the guy that came out with the rotary phone that was in stores a few years ago.


36. Tale of a Disturbing Internet Date

This happened last summer of 2016. A couple comes in, approximately in their late 40s, or early 50s. The gentleman proceeded to tell me they were here on an "Internet date" and he didn't realize his date was gonna be a “big black woman."

Needless to say, this was going to be my most awkward table all night. Why the lady didn't leave immediately, I will never know. They proceeded to order dinner and the guy made her order a steak, cooked the way he wanted it, and a shot of tequila. He also orders a steak and a shot.

He leaves for the restroom as I'm dropping off their drinks and she asks me if I could please call her daughter to pick her up. I give the number to my manager to make the call.

As I bring the salads and place them down, she explains she doesn't think the date is going well so she has called her daughter to pick her up.

He tells her she better put up when they leave because he's buying her steak for dinner. She proceeds to throw her tequila shot in his face. He pulls out a knife and threatens to hurt her and I have to restrain him across the table while the cops are called.

Several other staff, came to my aid until the police came in and arrested this guy. The woman's daughter came to pick her up. My co-workers and I bought her and her daughter dinner to go.


37. Mix And Match

I'm not a waiter, but this story is great. Two couples were going on a double first date. The four of them were all sitting around the table, and it was painfully obvious that their dates were dying.

The first couple got bored of each other within minutes, and the same with the second couple. After a while, the boy from the first couple starts talking to the girl from the second couple, and they hit it off.

But the other two on the date simply paid and left. The remaining two stayed for hours after their dates had left, just talking to each other.

They went on to have a second date, then a third, and ten years later they had me. I'm the result of a terrible first date. Thanks, Mom, for being bored of that guy. Appreciate it.


38. Icy Waters Of Regret

I went to the aquarium in Chicago on Valentine's Day a few years ago. It was super crowded (a line well outside the door) and super cold (10 degrees F with a wind chill).

In front of us in line was a teenage couple on a presumably first or second date and the poor girl was wearing a ball gown with opened-toed shoes.

I'm assuming both of them felt too awkward to just call it but they really should have just gone to a coffee shop or something when they saw the line. It was painful to see.


39. Bartender To The Rescue

I went on one of those "dating app nightmare" dates. Had spoken to the guy a few times, seemed nice. When I went in I asked if he minded moving to a booth, I didn't have a sweater on and we were by the door/window where it was really cold and he refused.

After that, he made a few racial comments that were red flags, admitted he lived with his mom and dad and kept trying to convince me he was really rich. The server/bartender was close to us (we were by the bar) and when he went to use the bathroom he came to see how it was going but he already knew.

We chatted for a little bit and he told me he'd rush the bill and that I should come back after the bad date leaves and have a beer on the house. When the bad date came back I said I wanted to get the bill and leave.

He walked me to a carport I said I parked and I left him there, he tried to kiss me but I dodged it. I waited for him to go away and went back with the bartender who was much nicer and it went 100 times better than the actual date.


40. First Date Snooze Fest

This was the first date. I had asked out a girl from one of my history classes. At the time, I did not have a job and was relying on my parents for food (housing and tuition were paid by scholarships). So I had no money to eat out, but I did have a couple of steaks in the fridge.

I asked the girl if she was okay with a home-cooked meal and a movie at my apartment. Amazingly she agreed. So I shooed all my roommates but one out (best friend/wingman that I couldn't kick out for anything) and made dinner.

I went to pick her up, and things were going great. I had previously learned that she had not seen the new Hobbit movie (2013, so the first one) and we'd agreed to watch that. I put in the movie, and we sit back and enjoy, poking fun at the movie, and enjoying it for what it is. Anyway. Now for the good part.

At the time I had wildly uncontrolled blood sugar levels, and in my nervousness had forgotten to eat anything that day except dinner. About 20 minutes from the end of the movie, I fell asleep, no warning, just out. Wingman, instead of trying to wake me up, laughs and takes a picture of my head on her shoulder, drooling.

At the end of the movie she wakes me up, I apologize profusely and expect to have an awkward class for the rest of the semester. I was so mortified I didn't show up to the next class period.

Well, out of concern, or some kind of masochism, she texts me and asks if I want to look at her notes for the class. We're married now.


41. A Physics Date To Remember

One of mine. I met a dude on a dating site, he was a graduate physicist student so pretty smart but equally socially awkward and didn't get out much. Also, kind of looked like Michael Cera.

Anyways, on the first date we met at a popular spot and sat at the bar which was mistake #1 because not a lot of privacy. So a lot of get-to-know-you talk but he was so awkward and kept talking about his work which went over my head because I don't know a lot about physics so it was mostly him talking and me trying to get a word in.

I had two beers and he had a water and I paid. No big deal but that was kind of awkward too. What's funny is I went to the same place with my current partner and I told him about my date there and the bartender was like, “Oh God, I remember that he was super awkward.” So it was so memorable, even she remembered.


42. Lost In Translation

I'm a waiter but the worst first date I've seen so far was my own. It sounded like an okay match, even though she wasn't American, she could still speak English very well and that's how our date proceeded at first. Both of us speak English. Sounds normal right?

She then started asking me questions in Vietnamese. I was having trouble answering them and explained that I was born here, so I wasn't fully fluent in the language. She started getting more aggressive with the questioning, in Vietnamese, and I was like, "Uh, okay, yeah?" Not getting what she's saying.

She then says in English, "How can you not know Vietnamese?" And I looked at her and said, "Well sorry we don't have any schools that teach Vietnamese here." She then starts angrily texting her friend and says to me, "I thought you were Vietnamese!" I say back to her, "Sorry, but I've lived here for the last 25 years."

After a long moment of silence, she tells me, "I don't want a family that can only speak English, when I come home I want my children to be able to speak to me in Vietnamese." I just sighed at how dumb the situation was, and quickly we split the bill and just left.

The person who arranged our date said to her that I was a Vietnamese man, which is true but I'm an American-born one, and the same person told me that it'd be fine if I didn't speak any Vietnamese because she was very fluent in English. I guess what we wanted got lost somewhere in translation.


43. A Married Man’s Revelation

I served at a restaurant bar. I get way into the whole making it a fun time for those who seem like they'd be into enjoying their time there. I could tell it was a first date because of how nervous each of them seemed to be. They were probably late 20's or early 30's.

Also, the guy showed up before the girl and was on his phone, and seemed nervous about that too. She got up to go to the bathroom at one point as all seemed well so I took my chance to snoop. I asked if this was their first date. He happily replied "Yeah" and told me how they'd each driven about 30 miles to meet "halfway." All is well.

20 minutes in, he stops me and asks for the check just a few minutes after getting their food. I jokingly asked "Uh oh. What did you do?" Guess that was the perfect question.

They get quiet for a second. I realize my mistake. He says "Well, It would seem she is not as okay with the fact that I am married as I thought she would be."

Still trying to keep my composure, I am curious so I go deeper yet and ask "Oh, well you're at least on your way out of being married, right?" Even longer pause and nervously laughs, “I should probably just get my check now. Sorry.” Douchebag.


44. When Size Matters

Man, I haven't thought about this in maybe 10 years. I was working the front desk, and this woman came down and said, "I need to talk to someone, you'll understand, you're a woman."

She was drunk, and nearly in tears. she had been seeing this guy online and they finally decided to meet in person, and they decided that getting a hotel room would be a good way to execute that.

Turns out, he has a small male organ, and now she's completely repulsed by this guy. But she's stuck with him, and she keeps finding excuses to come down to the lobby and talk to us. She just hates this guy now.  

Anyway, I think she left early, I don't remember, but I remember her walking out of the hotel with the guy at one point and kept thinking that his male organ must have been really small because it upset her. It made her emotionally unstable, that's how small it is. I can only imagine


45. A First Date Flashback

When I was 21, I was a waiter for a small restaurant little less than a year. At the time it was a pretty upscale place, and people frequently went there for first dates.

One night I walked past a table and inwardly screamed as I realized it was my high school boyfriend whom I'd dated for years. Until I abruptly broke up with him because of some messy emotional stuff I was dealing with had a terrible drawn-out and off-again phase for a few tortured months until we tried to go separate ways.

He was with a girl I'd never seen before and they were both dressed nicely. Awkward I decided the best course of action was to go up to their table and say “Hi” as I still had a very tender place in my heart for him and wanted things to be friendly between us. I went up to the table and said “Hi” to him and introduced myself to the girl who looked pretty confused and trod upon.

My ex just smiled this hard, fake smile and appeared to be in agony. I don't even remember what I said, but I kind of ran off abruptly mid-sentence to leave them to their meal.

It was pretty terrible. It's now six years later and we ended up finding our way back to each other and now we're married and fixing up our first house together. We both remember this awkward encounter very fondly now.