April 27, 2020 | Jess Silverberg

Waiters Share The Worst Dating Disasters They've Witnessed

Waiters see it all: the good dates, the bad dates, and the really ugly dates. Sometimes they watch from a distance, but other times they wind up directly involved in the chaos. Here are the worst dating disasters real waiters have witnessed:


#1 A Sad Ending

I was a waiter at a very famous, upscale restaurant and a gentleman approached me requesting someone take pictures of him proposing to his girlfriend.  After stalking the table for a solid hour, the moment was inevitably approaching. I set up at an angle she couldn’t see me and when he busted out the ring, I started taking as many pictures as I could.

Anyone who has tried to capture a once-in-a-lifetime moment on camera knows that you’re not really watching what’s going on, you’re just trying to frame the moment. After about 20 to 30 pictures, I slowly realized that she was declining the proposal and the scene was quickly degenerating into a five-alarm dumpster fire. However, I was far enough away that I couldn’t hear what was being said and I couldn’t be sure of what was transpiring, so I continued taking pictures just in case.

Finally, I stepped back and watched the scene unfold in reality as she stormed out of the restaurant in embarrassment and he scrambled to pay the bill and chase after her. He’d requested that I use my phone and send the best pictures to him. Needless to say, he never approached us for the pictures and I have about 100+ pictures of a wedding proposal gone wrong somewhere deep in my iCloud photobank...


#2 You Got Served

I worked at a bar in a hotel for five years. I had a table come down from their hotel room and sit at one of my pub tables for dinner. From the moment they sat down, you could tell the wife was furious about something. She was unbelievably pleasant toward me but she did not say a single word to the man at the table. I get their drinks and then their orders—he ordered steak and she ordered the sauciest pasta dish we had on the menu.

About 20 minutes later (the wife still hadn’t said a word to the man since they sat down), their food was done and my food runner set it on the table. Right as I was about to walk over to see if they needed anything else, I saw the woman stand up, say “Go screw yourself, John,” as she picked up the plate of pasta and dumped it all over his head and down into his lap. Then she very calmly walked out of the bar and back up to her hotel room.

I spent a few minutes helping the man clean up and got my manager to come to handle the situation from there as it was way above my pay grade at that point. Later in the night, the woman came back to the bar without the man and we talked for a while. Turns out, he admitted to cheating on her right before their dinner reservation. I never saw either of them again.

#3 Suspicious Behavior

I was a bartender at a country club in college and I watched a woman curse her husband out at their table because the husband kept flirting with the waitress. She got REALLY loud and walked out. Keep in mind, this was a nice restaurant at an upscale country club. The waitress felt it was all her fault but she told me the guy had been coming in there often and tipping her 100% of the bill every time.


#4 At The Country Club

I feel horrible because I never remembered anyone who worked at my country club but they had to always remember my name. They really do flirt with you though. And they would hire the prettiest girls they could find. Drinking at a country club was a mess. They don't cut you off and you can order whatever you want.



#5 This Is A Joke, Right?

I used to bartend at a yard house before. A yard house is a corporate place that's basically a nicer sports bar with a ton of drinks on tap with stupid, giant novelty glasses. I had a couple at the bar during happy hour drinking from one of the big glasses and they ordered some onion rings that were half price. He jokingly proposed with an onion ring and she started laughing, then jokingly said yes. Then he busted out an actual ring... she wasn't laughing anymore.


#6 A Happy Ending

I asked my wife to marry me. She didn’t say no or yes. She just brushed it off. A few weeks later, out of the blue, she jokingly said, “I’ll marry you–I need insurance and my job doesn’t offer it." I didn’t care what the reason was and I didn’t really believe the “insurance” reason, I was just happy she would marry me. As time went by, this started to eat at me, and about a year and a half later, she again, out of the blue, said: “You know I was joking about the insurance, I wanted to say yes the first time, but you caught me off guard and I was embarrassed. The insurance thing was a way for me to bring it up again, and get you to ask me again.” We’ve been together for 13 years, and she still has good insurance.


#7 The Hero We All Need

This happened when I was around 18 or so. I am mostly Native American—this is an important factor in the story. A guy and his date get sat in my section and he immediately asked to speak to my manager. This was before I even took their drink order so I was perplexed but went and grabbed him right away.

The dude then asked my manager for a "nice white server" instead. Right in front of me. While giving me a rather disgusted scowl. His date was so horrified she stood up and said, "Oh heck no. You can sit me at the bar sweetheart, this date is over." The manager made the man leave and comped his date's food. She left the manager $100 tip for me with a note that said: "You are beautiful and worthy of respect. Always remember that." Her date was a disaster but she made my night.


#8 Embarrassing Events

I used to work at a bar where 70% of the customers were on Tinder dates. There was a line of two-person booths along the wall when you first walk in. There were two dudes sitting by themselves in two different booths and both of them were facing the door. One was in the first booth, one was in the last booth. This girl came in and walked up to the first booth. She said hi to the guy, and sat down.

They were chatting for about five minutes when the other guy who was sitting by himself came up to her and said hey, I’m so-and-so… aren’t you so-and-so..? They all talked for like 30 seconds and she got up and went to sit with the other guy at the last booth. Eventually, a different girl showed up for a date with the guy at the first booth. I don’t know exactly what happened, but I almost died watching it unfold. She was definitely embarrassed.


#9 A Risky Prank

Not a waiter, but I saw a first date next to me. In short, the girl stated she has an allergy to pineapple, and the guy said okay in an "I don't believe you" kind of way. At some point, he scraped some pineapple glaze off his dessert and onto her spoon when she popped outside to make a call. She came back and ate her dessert without noticing too much... Then she had a severe reaction. The guy freaked out and tried to run but got stopped by my girlfriend who was suspicious of him. The manager administered the girl's EpiPen and the ambulance and police were called.



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#10 Calamari Disaster

One of my friends has a seafood allergy. She was getting to know her date and said from the beginning that she couldn’t have anything seafood-related. I guess the guy didn’t believe her? He ordered calamari rings but told her they were onion rings. The poor girl didn’t think twice and had a handful of them before going into a reaction not long after. No idea what happened in between that, but his reason for the calamari rings was because he thought she was lying.



#11 Wine-Stained Shirt

I worked fine dining in Vail, Colorado. I once saw a lady throw red wine all over a guy's shirt and leave. He sat and continued eating his spaghetti plate. No cares given. Other than following her immediately, it's not like he wouldn't see her right after the spaghetti. Vail is a mountain town with not much else going on around it. They were likely visiting and other than the car, there's likely no real place for her to storm off to that isn't just their hotel room or condo or wherever they're staying. Still, it was bold of him to sit there with a wine-stained shirt though.


#12 A Margarita Mess

A couple of friends and I went to the Mexican restaurant where another friend was waiting tables. There was a couple that was kind of catty-cornered from us that had a bit of an “off” vibe. We could see them, but not really hear them, so we asked our server friend what was up. She said it seemed to be a first or second date that was a bit awkward. The girl had ordered one of those enormous margaritas and was not sharing it.

I had to go make a phone call (back in the payphone days) and when I came back, I ended up sitting with my back to the couple. Maybe 10 minutes later, I hear our friend the server say, “No, no, no...” and the sound of a full punch bowl being emptied from a great height. The girl had stood up, swayed a bit, and vomited all over their meals, table, and the surrounding floor. The restaurant comped everyone sitting nearby, and the girl’s date abandoned her in the ensuing chaos.


#13 Consolation Brownie

I used to work as a hostess. A guy made a reservation at the most booked table. It’s by the window, all romantic, etc. Also, it was super visible from any other part of the restaurant. He came in, all dressed up and with a suitcase. Strange, but okay. A few minutes later, his date arrived. They laughed, flirted, and we actually thought it was an anniversary or he was going to propose or something, the way it was going. NOPE. Halfway through the evening, she started screaming at him. He broke up with her and actually packed her suitcase. Then he paid and left her there sobbing at the table alone. We got her a brownie on the house because just watching that, we felt freaking awful.


#14 Played For A Fool

This happened to a friend of my wife... She met a guy on a dating site. They agreed to meet at a strip mall parking lot and go to dinner together from there. He asked if he could drive her car because it was a Camero and he’d never driven one. So they went together in her car, to a restaurant a couple of miles away.

Dinner went okay, nothing too crazy. Then, he got up to go to the bathroom and never came back. After 10 minutes, she got up to check on him, and her car was gone. He'd dashed on the bill and stolen her car. She paid the bill, and got an Uber home, and called the police to report her car stolen. Turns out, the guy just left it in the parking lot where they originally met and seemed to think he did nothing wrong. Last I heard, he’s still being charged with auto theft.


#15 She's Got Issues

I'm a waitress in my father's restaurant. It's not that big, but we're usually full during weekends. A lot of couples come here because it's kind of "chic" for a french restaurant. Anyway, once there was a couple in their early-'30s. The dude arrived earlier than the girl, so I thought it was something like a date, but no... The girl ordered everything. She chose all the dishes, the dessert, and even the wine without even asking the guy what he would like to have.

They both didn't talk; they only said good evening to each other, which was weird for a date... But when I came to their table to serve the wine, they started to argue about their relationship. The dude was convinced that she cheated on him, and you know what, she admitted that and said very loud that he was bad in bed... At this moment, every single cell in my body was cringing. They kept arguing for 10 minutes until I decided to stop them because they were almost yelling and so disturbing the other people in the restaurant. The woman asked if she could have another bottle of wine, and she left within 5 minutes WITH THE BOTTLE.


#16 True Love

Not a disaster, but it could have been. A guy rented out a private room in the very fine dining establishment I work at. It was a dinner for two; a proposal dinner. He gave us instructions to bring the champagne when she said yes. I jumped the gun and poked my head into the room holding the champagne, just to check that I haven't missed it. The guy saw me, had a panic fit, and threw up all over the table. The woman was very concerned. She went over to see if he was okay. He pulled out the ring, dropped to one knee and proposed, with vomit still on him. She burst out laughing, said yes, and kissed him (on the head).



#17 Out Of Desperation

I was a bartender for a couple on a Tinder date. They talked for about an hour before he went to the bathroom, but he left his jacket on the back of his chair with his wallet and keys in. She stole them, stole his car, and then went shopping. That poor schmuck refused to call the cops for an hour because "it was going so well." I felt bad for him.


#18 That's... Impressive

This couple came into this bar that I worked at and it was business as usual. I took their order, brought out drinks and food, including dessert. Nothing seemed out of the ordinary. However, this couple began to argue as they worked through their dessert. Apparently, the guy didn't bring a battery pack to charge their phones. Homegirl was straight-up screaming at this dude. Luckily, it was a really slow night and they were only ones in the restaurant.

I offered to charge their phones. I NEVER do that because I don't like dealing with the hassle. But I felt for the guy because I was that guy at one point. This was the point where I felt like I should've thought something was up. The guy handed me what looked like a busted up prepaid phone you get from the supermarket and a chewed up charger cable. I ran to the back and went to charge it only to find out the cable wasn't compatible with the phone. I went back to them and noticed they left without paying. I was more impressed than I was upset.


#19 Temper Tantrum

 Couples fight in restaurants a lot. That, or maybe they argue everywhere. I couldn’t say. I worked as a waiter for years and I could not begin to count the number of arguments I saw. But one guy comes to mind above all of them. This guy must have been 50 to 60 years old and he got angry with his lady. He actually threw a snit and stomped off. He started wandering around the restaurant and looking back at her and scowling. It was like a child throwing a temper tantrum, but most children aren’t even this dramatic usually. It was nauseating to watch.


#20 Gold Digger

Bartender here. A couple on a blind date took their seats directly across from the dishwasher, so I had to pretend I couldn't hear him asking her: "Listen. I see you over there, just amazing and gorgeous, and I'm wondering what you're seeing in me. What do you think?" She cringed, made an effort to sidestep his questions, and tried to change the subject at least three times, while he ordered shots of Fireball (at an upscale establishment) for both of them. She would politely refuse, and he would end up drinking both of them. He didn't seem to be big on learning.


#21 Poor Guy

I watched a proposal in the dining room of the hotel I worked at. Everyone was eagerly awaiting the dessert and ring box to be brought out. She saw the box and just started saying no, and told the crushed groom: "We need to talk." People who initially were clapping just slowed to dead silence. She ended up going back to the room, collecting her things and leaving, while he cried at the table for a few minutes. It was super depressing for all the staff, guests, and that poor guy.


#22 The Boss Woman

My favorite was a couple who asked to be seated on the patio. They chose the furthest table from other guests. I went over to greet them with a smile and some good energy, and the woman locked eyes with me, saying: "This is not going to be a fun evening." The guy with her then tried to order a margarita and she said, "You can have a cola," and proceeded to order a Cosmo for herself.

They both got burgers. I went in to tell the hosts not to seat anyone near them, and for the next hour, this woman laid into the guy while he sat there and took it. Clearly, he had messed up in a major way. From the snippets I heard, she was explaining to him in great detail the way he had messed up, lost her trust, and it was over. She was incredibly civil, unflinchingly polite, and so confident. She finished, handed me her card, and walked away with him still at the table after she left me a solid 30% tip.



#23 Split The Bill

I kept my interaction with the table brief, but I'll never forget the time I had this one couple come in. As I was setting down the entree, the lady looked at her man stone-cold, pointed to his phone, and said: "So, who this tramp you have been texting?" Me, of course, being neither the tramp nor the texter in question, made definite haste away from that conversation. I do remember her asking to split the bill at the register though.


#24 Saturday At The 'Bees

I always wondered how the waitress at Applebee’s felt when I broke up with my ex at our table and she made herself scarce. At the moment, I hated being “that couple” but he left me almost no choice. I kept hoping the waitress would speed our meal along so we could get out, but I think she either was giving us space or getting the heck away from the awkward cringe table in her section. Now I think she either tells this story about us or had so many of these moments we were just another Saturday night at the 'Bees.


#25 Newbie Moment

I once had a couple that I didn't realize was a couple and once they were done with their meal, I asked if they would like separate checks. I honestly thought the woman was the man's mother and they looked at me with offended expressions. I replied, "Um... One check please." They're now regulars who come in almost every week and despise me. I was much newer to the job when this happened. I know how to read the table better. 9/10 times I just ask at the beginning if they want the bill split in any way if it's more than one couple. That way I know how to organize the bill.


#26 Rude Assumptions

I am black and my wife is white and I am ticked off whenever a waitstaff person asks if we would like separate checks. You would figure since this isn’t the '80s a waitstaff person wouldn’t do this. It automatically makes me cut the tip, and I am a great tipper. I used to be a restaurant manager so I know when stuff goes wrong it’s often not the server's fault. I would suggest defaulting to saying “One check?” and not make assumptions about the relationship.


#27 Barefoot Flirting

Not a waiter, but one time, I went to a decent restaurant and got seated next to a couple on a date. Not sure why our waiter chose that table when half the room was empty, but anyway, they were an elderly couple (probably in their '70s). The guy looked pretty humbled and the lady was completely dressed up. Bedazzled dress and everything. They had been flirting pretty hard during their appetizer, and when their dinner came, that’s when things hit the fan.

The man took his shoes off and was teasing the lady's legs with his toes. Then the lady took her shoes off too, and after a good round of footsies, the guy decided to massage her feet WHILE THEY WERE EATING finger food. I’ve never choked so hard. I swear I could see him rubbing right in between her toes. I just can’t imagine how they’re able to do that whilst stomaching their food.


#28 The Bridezilla

Not a waiter, but I used to be a banquet cook for large corporate events and weddings. I had your very typical bridezilla one weekend. She ended getting hammered at the reception and slept with a groomsman in the honeymoon suite. Needless to say, the husband left her immediately. At least I got a lot of compliments on my crab cakes.


#29 The Phone Rule

My husband and I have a rule that we don’t take phones out when we go out to eat. The one exception is if we’re looking up places to go next. But of course, in our case, we have kids and don’t always get to have the adult conversations we want to when they’re around. We tell the inappropriate stories from work, joke about things we have done in the past, and cut loose. Our date nights don’t come often so we like to make memories that don’t involve our screens.


#30 Novice Shrimper

I was a bartender at a restaurant that specializes in seafood. This couple came in and it was obviously a first date, they were both very awkward. They ordered a few dishes, one of them was a dish with Crystal Shrimps (peeled, without the actual hard shell, but still with head and whisker things and stuff). The guy proceeded to eat the entire shrimp. Like, head and tail and everything. It was as crunchy and horrible as you can imagine.


#31 Champagne Chaos

I saw a proposal take a turn when the guy put the ring in her champagne, she drank the champagne quickly unknowingly and started to choke. The guy performed a Heimlich maneuver and the ring pops out only to fly into someone else's food. The gguy had what appeared to be two heart attacks but in the end, the lady did say yes. Side note: because of the almost-death, they got a free dessert and they laughed about the whole evening saying "till death do us part for real" and they wanted no beverages at all unless it was super clear and if the guy didn't order it.


#32 Almost A Disaster

Not really a disaster, but a funny story: I was a waiter at a nice restaurant. I got two young people on a first date. The girl said to me at some point that she had a seafood allergy, then the guy ordered seafood right after that... it took him a couple of seconds after I asked him if he was sure it was a good idea (with a knowing look) to understand what I meant! He ordered some chicken. (You know... you really should not kiss someone who ate seafood if you have an allergy to that). I hope the rest of the date went well for them after that.


#33 The Other Man

Oh, I worked at a fancy place, so I saw a lot. The worst was when this guy got down on one knee to propose... just as this other guy came in and his girlfriend told him that she was leaving him for the other guy. They had been having an affair for six months. They had invited him out so he hopefully wouldn't make a scene. The two of them left him at the table, sticking him with a $200 bill. We all pitched in to pay it and bought him a couple of drinks.


#34 The Lost Bet

Not my story, but my partner just told me about this happening at his work. We live in a pretty large university college and one time a guy came in with a plant for a date. He sat with it at the table, ordered it food, drinks, and dessert. He was a total gentleman to the plant. Turns out he lost a bet with his frat brothers.


#35 Read The Room

I worked briefly as a waiter at a semi-nice place near me. I had a couple come in for a date who we've seen there a few times before (I think it was their regular dating place). She was very clearly sad and was talking about how her uncle was really sick and was probably going to pass away soon. He decided to pull out the ring and pop the question anyway. Seriously, dude? Read the room.


#36 Take A Hint

I was serving in a French restaurant, small but upscale. A couple came in and everything about the two screamed the first date. He was trying to impress his date by ordering the appetizer in a French accent. He ordered the corkage fee as it was the cheapest item on the menu. I tried playing it off and giving the dude an out by asking him if he'd left the bottle with the host or bartender but he wasn't getting the hint. His date was though and was laughing into her napkin. When he finally figured it out he was so embarrassed that he practically ran out of the restaurant. His date was still hungry though so I comped her an order of duck and we traded some great jokes at the dude's expense for the rest of the night.


#37 Ghosting The Bill

Not a waiter, but I once witnessed a woman ghost her date at the end of the night. It was a fancy jazz club, and the couple racked up what I assume was at least a $500 bill (there was a TON of wine and they went through a few expensive entrees). When it came time to pay, the woman snuck out while the man was in the bathroom, and just disappeared. The dude was distraught.


#38 Red Flag

Not a waiter, but I saw a couple at dinner and couldn’t shake the feeling that this was an escort scenario. She was clearly out of his league and much younger—so far so good. But then it became obvious that he did most the talking, bragging really, and she laughed at every single attempt of a joke. It was awkward to watch and became so apparent that our entire table noticed (I was out with three friends, we sat next to them). I know this could also just be a gold digger situation but there was something about them that made it feel like she was professional and he had no clue what he was doing.


#39 Sticky Drinks

I wouldn't say it was a disaster but once my coworker came up right next to me with a whole cabaret full of drinks (mostly pints). Then, I suppose she tripped or lost her balance or something because suddenly the content of her cabaret was all over me. I was dripping with sticky drinks... right in front of my boss. She said not to worry, she saw the whole thing and it was an accident. I just asked her if she would have my back in case some customers complained that I smelled like drinks.


#40 Soap Opera Fight

When I was 16, my aunt was organizing a wedding buffet and hired me for the night as a waiter and helper. I was attending the back tables when I woman with to little dress and too many drinks, yelled: "You should have married me instead! Screw her!" Cue a full soap opera girl fight: the bride, pulling hair, throwing red wine on the white dress, slapping her face.


#41 Second Time's A Charm

Not my story, but a story from a friend. So one night, she was waiting tables, and the guy was proposing to his girlfriend. And guess how... by putting the ring into her drink. Don't worry, she didn't end up drinking it. Luckily, she caught it, but the guy got chewed out when she saw it. My friend was there to watch her scream at him.

Girl: "You jerk! If I swallowed that, I could have ended up going to the hospital! That could have ended up more than the wedding if stuff had gone wrong." Yeah... safe to say, she didn't say yes. That time. But the next time, luckily the guy learned and proposed by kneeling onto one knee. That time she said yes.


#42 Spilling The Lemonade

Not a waiter, but I work at Panera. This one guy came in with who I assumed was his girlfriend or wife. I took their order and they sat down. Maybe three minutes later, another woman walked in. She didn't notice the couple at first. She went ahead and ordered her food. She also bought a bottle of lemonade. She paid, turned to sit down, and saw them, dropping the lemonade and spilling it everywhere. It turned out, SHE was the wife, and the lady the husband had come in with was his mistress. So naturally, there were some crosswords exchanged. All three were asked to leave and I had to mop up the lemonade.


#43 At Least A Facepalm

My friend bartended a couple that I was serving (we sat them at the bar and she wanted me to serve them). Anyway, the guy ordered mushrooms for them, and as soon as he even finished saying the order, his date said, "But I'm allergic to mushrooms," to which he replied, "It's okay, I can eat em all." He did not make out with her soon. Maybe not a disaster but a facepalm at least.


#44 Left Alone

I had a couple come in and they were clearly in the middle of a fight right off the bat. I greeted them and the man told me to go away. I watched him berate the woman for about five more minutes and they ordered drinks. I brought them, asked if the wanted to order, and he told me to go away again. Then he got up yelling, threw a few coins at the woman, and stormed out. I watched her try to count out the change he threw, and what she had in her purse to pay for the drinks, but she clearly had nothing. I took the small tab, said don’t worry about it, paid it myself, and she left. My coworker said she saw her on the road alone later that night. It was a pretty sad situation.


#45 No Faith In Humanity

 I work at a trendy bakery in town. There was always a line out the door on Saturday mornings...  Someone came rushing in once looking for a doctor because a man just got hit by a car. There was actually a doctor in the line who ran out and called 911, etc. The doctor came back ten minutes later to get back to his spot in line and the people DIDN'T LET THE DOCTOR BACK IN HIS SPOT. My faith in humanity is dead sometimes.


#46 Offending Karen

I was at a restaurant once and this couple walked in. They started talking and I heard the woman bring up adopting a child. The guy said, "I don’t think we are ready," and this set off the people next to them. This lady, let's call her Karen, suddenly stood up and poured her smoothie on the guy, saying  “I can’t believe you would say no to adopting a child!” And he smelt like apple, banana smoothie the rest of their date.


#47 Touching A Nerve

I have one. I was a server at a wine bar several years ago and on a particularly slow night, an older couple came in. They sat in the corner and talked until closing time (10 pm for this day). When they asked for the check I (maybe stupidly) asked if it was together or separate. The lady broke down crying and the man told me that they were finalizing their divorce. I have never felt so awkward in my life.


#48 Dodged A Bullet

A guy I know who is a waiter told me this story. He saw a man in a suit obviously looking nervous. He was clearly on a date. Then his date came in. The dude started looking super excited and happy, and then his smile faded in seconds as he noticed she brought two kids with her. He left without saying a word. That guy dodged a bullet.


#49 What's With Lemonade

I have a lot, but my favorite was this: I had a couple sitting in our patio area. They were arguing the whole time. Just as I arrived with the food, the man stood up, took his full glass of lemonade, and threw it in her face. He told her to have fun walking home as he just left her there. She started crying I felt bad and helped her as best I could. I even called her a taxi.


#50 Flying Yellow Rice

A lovely dressed gay couple came in and all was fine. I made their drinks and sat them down. Everything seemed fine. Suddenly one of them threw an entire plate of yellow rice at the other person's head and there was yelling. No tip AND I had to try and get the rice out of the booth cushion. I wasn't close enough to their table to hear what was going on, but it must have been bad for that to have transpired.


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