There are bad dates and then there are BAD dates. Bad dates that will go down in infamy for their terribleness. Since servers see a lot of dates they're bound to see the worst of the worst. People might think the servers would be safe from the awkwardness of the date, but they'd be wrong. These dates are so bad, they leave everyone in the restaurant cringing for the rest of the evening.
Content has been edited for clarity.
A Crazy Twist
“I watched a guy proposing to his girlfriend. She said she couldn’t marry him because she was pregnant with his brother’s child and she loved him more.
I was shocked when they didn’t leave right away, they had a nice dinner. She ate, he cried. Then she told him she didn’t have any money so he paid. Then she told him he had to be out of their shared apartment by tomorrow afternoon because his brother was moving in with her.”
I Feel Like There’s A Wall Between Us
“I worked at an upscale seafood restaurant for about a year. One particular woman would bring in a different date each week, and every single time she was there, she would erect this barrier between her and the date. I’m talking salt and pepper shakers, menus, dishes, drinks.
Whatever she could get her hands on, she would construct a physical barrier out of and then carry on with the date as if things were completely normal. The confusion and distress on the faces of the men she would bring in was always my favorite part of Saturday night.”
Straight To The Point
“Dude came with his wife, little late for their reservation. No problem, it wasn’t busy. So I sit them down, offer some drinks etc. They order a bottle of the most expensive drink we have. Wow, okay…Well as the time goes, the food starts to come out for them, and as I walk to the table the dude tells his wife with a straight face: ‘I’m leaving you. I’ve contacted a lawyer, he should speak to you soon.’
She was shocked, but kept it together while I awkwardly put the food on the table. As soon as I left, she stood up and went towards the bathrooms. Dude called me over, he paid the bill, got up and left.”
Crash And Burn
“I had a guy order all the expensive drinks, appetizers, the best entrees on the menu, a luscious chocolate mousse cake. At the end of the meal when I asked if there will be anything else, this guy says to me, ‘What can I do to guarantee I’ll get laid tonight?’
His date turned beet red and gap jawed. I said, ‘I think you were pretty much well on your way… until you said that.’
His date just said, ‘Yup.'”
First Date With A Liar
“I worked at a pizza place in the mid 90s with old school red booths and a sit-down Pac Man game.
A young couple in their late teens came in and sat down. It was already after 8 pm and they had apparently gone to a movie earlier as they were talking quite loudly about it (‘I know, wow, right?’).
They order a supreme pan pizza (pepperoni, beef, pork, green pepper, onions). I ask if they want everything on the pizza and they both say yes. Less than 15 minutes later, I bring it out and serve the first slice to her then a slice to him. Ask if everything is good and walk off to get some more drinks for them.
I hear him yell, ‘Why does this pizza have onions on it?!!!?’ from across the dining room. Of course everyone stops to look, including me. This kid is standing on the booth, yelling at me. Immediately, I walk back with their refilled cups to see what the problem was.
I get back to them and he immediately goes into a tirade about onions throughout the pizza. I apologize for the onions and offer to get a new one made. Instead, he starts yelling about the green peppers and how they are super spicy (yes, bell pepper is spicy according to this guy) and I was just trying to make his night horrible. I look over at his date and she has her face in her hands.
I rush to get a new pizza made for them, this time I confirm every item on the pizza and get it comped by my manager who was sitting in the back laughing at the absurdity. She finally goes out there to talk to them and this guy yells at her. I look their way and the girl is sitting with her face in her hands again.
The new pizza comes out and my manager and I both walk it out and again, I serve the first slice. He immediately goes off that the pizza is too hot and will cause injuries. My manager tells me to go away while she handles it. This time the girl gets up and walks towards the restroom. She stops me and apologizes for his behavior, that it was their first date and he bought a lot of stuff at the theater.
I immediately understand what he is doing, he doesn’t have any money so he is trying to get free food for his date. It worked.
My manager has gotten him to stop yelling and the young couple has started eating. They finish and get up to leave. She starts yelling at him for not tipping. He says I didn’t deserve a tip after messing up so much. She calls him out for being a cheapskate and tosses some money on the table and walks off. He picks up the money and pockets it.
Out in the parking lot, she starts yelling at him again. She walks in and asks if I got my tip, of course I answer no and she storms out again. Yelling at him for stealing. She walks back in dragging him behind her by the hand and forces him to give me the tip and apologize.
I don’t think there was a second date.”
SOS!
“It was clearly an internet date and the guy showed up first, looking excited. Twenty minutes later, a kind of busted looking woman came in and sat down with him. They were my only table at the time so I was paying pretty close attention to them. They each ordered a drink and before he’s halfway through his, she orders another. And another. And another. He’s looking at me kind of desperately at this point but there’s not too much I can do except keep a close eye on her behavior.
She starts crying after the 4th drink and tells us BOTH (!!) that she just got dumped last night. Both the dude’s and my eyes are wide and I excuse myself politely. They eat, sort of, and she orders two more drinks. He asks for the check at the end and I bring separate ones. He tips 100% and gives me his number. She pays in exact change.”
Shutterbug Mom
“Ice cream shop employee, so not quite a waitress, but the couple were at least 16 and were being chaperoned by the girl’s mother, who insisted on taking photos every few minutes.
Not just candid photos, but posed ones. Taking their ice cream and getting out the door with it took nearly 20 minutes because the mom wouldn’t stop.
The girl seemed pretty embarrassed by her mom’s behavior, and the boy looked immensely uncomfortable with the whole situation.”
Don’t Put A Ring On It
“I worked at a bar that was a notorious pick up joint. This guy was sitting at the bar and I noticed him take off his wedding ring as soon as he came in and sat down. He started talking up this woman, it was getting near closing time, and they were getting ready to leave, together.
I asked one of the male bartenders to borrow his wedding ring for a minute.
As the guy and the girl were getting up, I put the ring on the bar and said, ‘Is this your wedding ring? I think you may have dropped it on your way to the bathroom.’ He turned beet red and she ended up leaving without him. She did thank me, though.
He had already signed their tab and given me a tip. Not that it would have stopped me from doing it if he hadn’t already paid. I made bank at that place on Saturday nights.
Incidentally, I witnessed several of my friends’ boyfriends come into that bar with other women. A few walked out when they saw me, but most didn’t. Call me a snitch, but I told on them every single time.”
So Enchanting
“Once my husband and I went on a date to a Greek restaurant. The waitress who seated us mentioned that the couple at the next table were on a blind date. The tables were close enough that we could hear their conversation.
The woman spent most of the evening talking about her dead daughter and how she had died. She had drowned a year or so earlier. Not that I think she should be ashamed or afraid to talk about her child, but it was a pretty heavy topic for a first date, and a blind date at that. At the end of the date, as they were leaving, I heard her say, ‘Have I scared you off?’
And the guy replied, ‘No! I’m enchanted.’ So strange. I still wonder about them sometimes, and if they ever went out again.”
Awkward For Literally Everyone Involved
“I work at a dinner theatre, and we usually do proposals where we set up a ‘random draw’ where the ‘winner’ comes up on the stage to win their prize, and are then surprised by their partner who proposes. It’s usually sweet and makes everybody in the room all fuzzy and warm.
This one guy wanted to take it further and requested to perform a song — he brought his own music and everything. We’re pretty easy going at this job, so we agree to let him do it.
We do the fake draw, the woman comes up on stage in front of a room of 400 people, and the music starts to play. Apparently, this guy was a little nervous, and he compensated by having a few drinks. So what follows is a slurred performance of a song written by this guy, that seemed to focus on how he was sorry for cheating on this woman with her sister and at the end of it, he gets down on one knee and proposes. Usually, this gets a round of applause, encouraging the person to say yes; but not after that train-wreck of a performance. The poor woman was just holding her face the entire time and starts shaking her head and says ‘No, what’s wrong with you?’ She storms off and leaves him and our stage manager on stage to a bunch of murmuring from the audience. The only thing our stage manager can think of to say on the mic is, ‘Well, that’s that.’
The guy ended up staying for the rest of the show and had many more drinks. That was years ago and it still remains one of the cringiest things I’ve ever seen.”
That’s Not A Compliment
“I worked at a Starbucks through university, so I saw my fair share of dates. The most memorable one involved this girl in maybe her early 20s. She came in first, dressed up in this nice little black dress, and sat at the 2 person table near the front till where I was posted. This girl was probably 5’2” or so, and 120 lbs give or take.
Maybe 5 minutes later this guy comes in, wearing what looked like normal street clothes. He came over to the table and the girl stood up, and I kid you not, the FIRST WORDS OUT OF HIS MOUTH were, ‘Wow, you’re skinnier in person.’
I’ve never felt so embarrassed for a complete stranger in my life. And yes, the following date looked as awkward as you’d expect following this. The guy basically talked about himself for maybe 30 minutes, with the occasional ‘Uh-huh’ from his date, and then the girl left.”
A Violent Date
“We had a couple come in and sit at the bar. The meal was going fine and then suddenly the woman stands up and pours her drink on her date’s head.
The man then takes this as an opportunity to grab the woman by her hair and start punching her over and over in the face. Every man close by in the restaurant stood up and worked to get him off of her. Realizing he was outnumbered, he stormed out. Police were called. The woman was comforted by employees in the waiting area until they came. I was 16 and vividly remember picking up broken pieces of makeup flung from her purse all over the place.”
A Pawn In Her Game
“This girl and guy came into the restaurant I used to waitress at and I could tell right away she wasn’t into the guy but that he was really into her. She was on her phone the majority of the time, and every time I’d walk past or go over to them, she was talking about an ex. She even asked me to take a picture of them and she said she was going to post it for him to see.
When I would see him talk, she either didn’t seem to notice because she was on her phone or would just nod/shake her head. The guy looked so uncomfortable. He seemed really excited at the start of the date, but I could tell how disappointed he was by the end of it. She didn’t seem interested at all, and it was clear she had gone out with him just to tick her ex off.”
Bad Trip
“I had a regular come in on a date and he is usually a laidback and chill guy but I guess he was nervous or something because he came in as high as a kite. He kept telling the girl how beautiful she is and kept repeating happy and lucky he was. I guess the girl couldn’t handle it anymore because she just booked it before food came out.
Then my regular started rampaging through the restaurant and stomping the floor really loudly and he tried to go into the kitchen and my coworker tried to stop him. He got pretty hostile and tried to fight my coworker but I stepped in and told him that customers weren’t allowed in the kitchen and he went from 100 to 0 but went back to stomping around the front of the restaurant. My boss came out to see what the commotion was and ended up telling the guy to leave. He tried to fight my boss but he left after my boss threatened to call the police. I never saw that guy come in again after that incident.”
An Adidas Track Suit
“I was out with hubby and my best friend at a restaurant best described as casual fine dining: a suit and tie wouldn’t seem out of place but they still do happy hour.
We’re on the patio having dinner and working our way through the drink menu (for some reason we decided we wanted to sample all 12 drinks that night) when a woman gets seated near us. Waitress tells her that she’ll bring her companion over when he arrives. She’s dressed pretty smartly, black pumps, black pencil skirt, blush colored blouse- very businesslike. Her date on the other hand arrives about 5 minutes later wearing a matching pants/jacket navy blue Adidas track suit.
The woman looks pretty mortified but sticks it out and we get to hear a few snippets of the conversation as we enjoy our drinks. The guy spends the first 30 minutes talking pretty much non-stop about everything under the sun and then STARTS SAYING WHAT THEIR KIDS WOULD LOOK LIKE…..
This lady starts shooting my husband these pleading looks of ‘help me!’ so when she excuses herself to go to the washroom for the 4th time in under an hour, my best friend and I follow her to ask if she wants to be rescued.
She ended up deciding in the bathroom that the date was over and actually went back to the table to thank him for dinner before paying their entire bill and leaving. Guy had been talking so much he was only half way through his entree but she told him to stay and finish his meal. He even tried to go in for a kiss as she was saying farewell but she saw it coming and turned like a Jedi to avoid. After she leaves, he pulls out his phone and calls HIS MOM to tell her that he just had an amazing date with this woman and he thinks she might be ‘the one.’
Don’t think I’ve ever laughed so hard in my life.”
Catfight
“I saw these four people on a double date. It look like the boys were best friends and the girls hated each other. The boys sat on one side of the booth and the girls on the other. You could see the anger in the girls’ faces and the best way I can describe it is passive-aggressiveness toward one another.
The boys were having a great time talking with one another and the girls were not having it. Once the date was over, the girls were almost catfighting but still kept their anger within, I still can’t get the looks of each of their faces off my mind.”
A Strange Exhange
“I worked at a Ruth’s Chris and had this couple come in and sit at a private booth in the corner. The guy was in his late 40s/early 50s and dressed pretty flashy and the girl was in her early 30s and pretty attractive and put together.
He bought her something from Tiffany’s and she thanked him, put it back in the box, put the box back in the bag and placed it beside her in the booth (rather than wearing it). She ordered steak and lobster and had probably 4 bites. The guy ordered tons of drinks and asked me what kind of shots we had (?). He was really trying to create a fun party atmosphere and she was pretty straight faced (playing the superior card). At the end of the night, he invited me to come join them ‘for a drink’ in their room at a very upscale hotel nearby. I declined (after he paid of course). They left and some time later he came back in because she had forgotten her Tiffany’s bag.
The next morning I was out for brunch at a pub and saw the chick in a velour jumpsuit laughing and talking jovially with another guy.”
A Lover’s Spat
“This one actually happened today. I’m a host, which is actually important to this story. So I work at a local steakhouse, and today a couple comes in, they ask for a table for 2 and I seat them, all seems fine so far.
About 10 minutes later the bartender calls me over, and says they were asking for me. Me being the naive 15 year old I am, thought they were going to ask about my age, as most people do, but no. I get over there and the woman says to me, ‘Can you find this man a place to sit?’ and she points at her date, I was confused so I ask to clarify, ‘Him?’ and point at the guy she walked in with.
He looks up at me, pain in his eyes, and says, ‘No we’re fine, thank you.’
She cuts him off and says, ‘No, we aren’t fine (His name,).’ She turns to me again, ‘Can you please find him another place to sit?’ I ask him if he wants to move, he says he’s fine and tells me it’s cool if I walk away. They go back and forth like this for a bit before she turns to me and says, ‘You know what? We are fine, thank you.’ So I walk away.
Not even 30 seconds later, she grabs her stuff, and just walks out. Obviously she was freaking furious. So I go to the waiter that WAS assigned to them, and asked him if he knew what was up, and he tells me that he took some drink orders from them, and all seemed well, a house Cabernet for the lady, and a Coors Lite Draft for the guy, a few minutes later he brings them their drinks, and they’re in the middle of going at it. She says to him, ‘Just get the heck off your phone, (His name,) we can move somewhere else if you don’t like this spot.’ The waiter asks if they would like to order their food, but they ignore him. So he leaves, assuming they’ll work it out themselves. That’s about when they called me over.
First time something like that has happened to me, it was SO uncomfortable but I’m glad to be out of it.”
Heart Break On The Menu
“This guy came in and ordered a water while he was waiting for someone. He seemed pretty nervous. Soon a girl comes and joins him, they seem familiar with each other. They eat dinner and order some dessert.
I come back to check on them and she looks like she’s about to cry, so I turn and go to another booth. I give it a few minutes and when I come back she’s gone and he has his head in his hands, dessert basically untouched. I felt SO bad having to give him his check. He just kind of smiled at me and I didn’t know what to say so I told him, ‘I can put that it a to-go box if you’re looking to leave. But you can stay here as long as you need to.’ He just nodded. I brought him a box and he left about 5 minutes later.”
Don’t Do The Waiter’s Job
“I was a new server waiting on a large party. Of course, everyone wanted water, so I came out with a large tray of water glasses.
That tray was balanced. The weight is equally distributed so that the tray is easy to carry. I start passing out waters, but one guy reaches out and takes a water glass for himself and messes up the balance of the tray. The remaining six glasses of ice water tip behind me, and all of them fall on a girl at a two top table…in a white shirt…on a date.
She wasn’t just a little damp. She was drenched. I felt awful and she was mortified. Her date had no idea what to say, and all I could do was apologize non-stop and go find her a towel.
Moral of the story… let the waiter hand you your water glass.”
