Waiters And Bartenders Reveal The Worst Dates They’ve Witnessed

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One man, one woman (or one man, one man; one woman, one woman; you get the point). A bar. Alcohol. What could possibly go wrong? As it turns out: quite a lot.

It was Shakespeare that first wrote that “The course of true love never did run smooth”, but it’s unlikely the Bard was ruminating on the possibility of a grown man defecating in his underwear, while on a date, because he had inhaled too much liquid courage.

iStock / gradyreese

Some dates are so bad that, irrespective of their comedy value, those that endured them would never dare retell them. Luckily (or unluckily, depending on your standpoint), there’s no such thing as bartender-client privilege, and these bar-people are ready to tell all. Enjoy.

The Party Trick

“I was working in bar called Off Broadway, and this couple was sat at the corner of the bar,” says Felix Cohen, owner of Every Cloud. “The date’s clearly not going very well, and after about 30 seconds of silence, the guy gets his phone out, and with a chest puffed out, ‘This is my party trick’ vibe, says: ‘Ask me any math question, and I’ll work it out quicker than you can do it on your phone’. The girl looks at him, blankly, like, ‘What the heck are you doing?’

iStock / gpointstudio

“Maybe he was reaching deep down, trying to find that one trick that would help him out. Perhaps it’s something he did at some point on every date. Either way, it was just spectacularly bad. Obviously, the girl was like ‘No?’ but he insisted. She asked one, he did it wrong, and was way slower than a calculator. Five or 10 minutes later, the date was over and they were going their separate ways.”

Unwanted Company

“This was six or seven years ago,“ Cohen shares, ”and wasn’t a date as such, but I vividly remember it being a horribly awkward interaction for everybody involved. A nice lady, who I’d been chatting to for a lot of the night, was sat at the bar, and this banker guy in a suit comes along and starts hitting on her—to the extent that she’s visibly uncomfortable.

“I just said, ‘Sorry sir, I think you should go and talk to someone else, this lady is having a night out on her own’, at which point he absolutely flipped on me, saying, ‘Don’t you tell me what to do—I make more in a day than you do in a year.’

iStock / Bogdanhoda

“The thing is, for my day job I work in tech, so it was quite nice to turn around and say ‘You don’t—I’m CTO of a fairly large organization, and I do this for fun. Also, the bouncer is behind you, so you can leave now or be dragged out.’ I don’t remember it word for word, but that was pretty much the vibe.

“There’s this assumption that service staff are beneath you, and even if it’s something you fervently believe, it’s such a dumb thing to actually act out on because, best case scenario you’re gonna get stuff done to your food and drinks, or get kicked out, so there really is no point.”

Wingman Woes

“There are a lot of single people, young professionals aged around 24 to 35, in the Clapham and Balham area [in London],” shares Craig Gordon, owner of Home SW15. “So we organized a ‘Taste and Date’ thing, where after each course people would rotate to the next person, have another plate of food and glass of wine. Ladies tickets sold out straight away, and the guys’ ones took a lot longer.

“In the end it was just remarkably awkward, and there was one guy I’ll always remember who said nothing. Every time he moved round; nothing. There was the odd yes or no, one word answers and no questions back. He was frozen and completely disinterested, it was the most cringeworthy thing I’d ever seen.

iStock / Steve Debenport

“He was tiny, wore a suit that was too big for him, and clearly his mate had signed him up for it. You’d have 10 minutes per date, and to eat each plate of food, but 10 minutes can seem like an awful long time in those situations.

iStock / Highwaystarz-Photography

“He finally got chatting to one girl towards the end, which I think was a combination of finding her attractive and having had a glass of wine with each course. When the event had finished his mate arrived – either to collect him, or see how he got on – and ended up getting with the girl. The one girl this guy has actually spoken to, and she leaves with his friend.”

A Stand Up Guy

“A lady came to the bar, and explained she was waiting for a man,” said Fredi Viaud, bar manager at Home SW15. “After a few minutes her date arrived, they started to get to know each other and ordered bar food, cocktails; everything. You could see that he wasn’t feeling at ease, and that maybe she was trying too hard. They weren’t arguing or anything, it was just quite awkward.

“This carried on for about an hour, then when the lady went to the toilet, he just disappeared. Stood up and left. When she came back he obviously wasn’t there, and he’d left without paying the bill.

iStock / filadendron

“The funny thing is, she’d been the one that ordered—a couple of cocktails each and some bar food, maybe $50 worth—and I think he didn’t like that she was ordering for him.”

Just Not Worth It

“This girl came in and ordered a pint; it must’ve been a good 20 or 25 minutes before her date arrived,” says Matt Smith, a former bar manager. “She had finished her drink and was about to move on by the time he sauntered in. This guy was typical ‘bro’—loafers, no socks, upturned trouser and slicked back hair. He was even wearing sunglasses, at 8:30 at night.

“He sat down and ordered a white wine, which doesn’t really go down well, because our wine list was ‘red, white, or rose’, and you could tell she was not impressed. They were both sat on bar stools, and she was legs crossed, arms folded, no f*cks to give, whereas he was slumped on the bar, as if he’d had the hardest life.

iStock / SolStock

“She managed a second pint, he asked for a Dark and Stormy—in a pub that barely had ginger ale—and eventually she just said, ‘This isn’t worth it, goodnight’ and walked out. There was no scene, no flipping of tables, but she said it just loud enough that the bar staff could hear.”

The Accident

“The pub I ran served traditional real ale and rough-cut cider, and some people couldn’t handle it very well,” Smith shares. “On more than one occasion, men and women have damaged themselves and, let’s say, left the evidence behind.

“This one night, I vaguely knew the girl that came in—she really liked the place, was really pretty, and would often bring dates there. On this particular night, she brought a guy in and it was all going fine, until [the guy] suddenly rushed to the toilet and she was on her own for 10 or 15 minutes.

iStock / SolStock

“He came back and asked to leave, so a staff member thought they better check the toilet. Turns out someone had stashed a pair of soiled boxers behind the only toilet we had. He’d been on the cider, as that’s what she was drinking, and clearly tried it, liked it, but couldn’t handle the fact that a drink that tastes like apple juice, but is 8 percent.

“As his [dirty] pants showed, the cider made him a bit squiffy. It’s not that uncommon—cider is particularly notorious as it contains a living product, and because of the yeast and sulphites and whatnot, it just really doesn’t sit well with some people.”

The Mansplainer

“This happens way more often than you’d expect—or perhaps you do expect it—men explaining jokes to women, that they’ve made, when the woman has clearly understood the joke; it just wasn’t very funny,” says Cohen.

“On this occasion, it was so excruciating because there was like a slight race element to it, or he’d done an awkward accent, and she was like, ‘Yeah, I get the joke,‘ but he kept explaining it. There was like half a smile at best.

iStock / SolStock

“I don’t remember the joke, but it was awful, either taking the piss out of a Yorkshire accent or possibly slightly worse—attempting a Jamaican accent or something. I just remember being mortified by the whole thing.”

The Tabasco Shot

“Okay, so there’s this one date that probably doesn’t show me in the best light,” Smith admits. ”A guy called Martin brought his boyfriend in, and I knew Martin pretty well so I let them stay for a lock-in. Problem was, his boyfriend had a massive attitude.

“I offered everyone a shot, and there was a particular shot I was known for called a Mad Dog, which is vodka, Tabasco and blackcurrant. I actually quite like it, and it went down fine for everyone except the boyfriend, who proceeded to vomit all down the walls and had to be escorted home.

iStock / Rawpixel

“Next time I saw Martin a few weeks later, they’d broken up. It wasn’t my fault, I believe I just highlighted a flaw. That being said, I did put quite a lot of Tabasco in his one.”

We simply couldn’t get enough of this awkwardness. We went to Reddit to find more horrible date stories.

We cleaned up the very best stories for grammar and readability, and we now present them to you in all their cringeworthy glory.

Hand-kissing is as outdated as the dinner date.

“[A] couple in their mid-twenties comes in, it’s obviously a first date, but they seem to really like each other and are getting along well,” wrote foppishyyy. “I wasn’t serving them. However, I was serving the table next to them. About halfway through their meal I notice them holding hands over the table. Cute. Then the guy lifts her hand to his lips and kisses the back of it.”

Okay, all’s well. Until…

“[It’s] bit of an outdated gesture, but still cute, I guess,” the Reddit user continued. “The woman seems slightly confused but goes along with it. A little while later, I see the guy do it again. Okay, dude. Then again. [The] woman is confused and looks a little uncomfortable. They are no longer holding hands.”

istock.com/Artem Tryhub

Uh oh. You’re not going to like this finale.

“I go to serve my table and see the dude full on making out with her hand, tongue and all,” wrote foppishyyy. “[The] woman looks extremely embarrassed and uncomfortable, looking everywhere but at her date. I go over and casually ask if they need anything, and the dude stops. [The] woman yanks her hand back. She left pretty soon after.”

That’s…probably the right move.

Don’t forget: Ghosting is always an option.

We tend to sympathize with ghostees and vilify ghosters. When it comes to first dates, though, anything goes. Restaurant servers have seen their fair share of spontaneous disappearances

“This isn’t as bad as some of the others,” wrote lachrym0se.

We’ll be the judge of that.

“The guy and girl arrived separately, and it seemed like they were meeting for the first time at the restaurant,” the Reddit user continued. “They sat down, then the girl excused herself and went to the bathroom.”


“The guy ordered drinks for them both while she was gone, then, after like 30 minutes, ordered two meals. It was so obvious she wasn’t coming back, but he kept calling her and eventually just left all the food and drink untouched and paid the bill.”


There’s a bit of a mysterious ending to this next one.

Here’s a great story about why you should keep things casual on a first date. That is, no expensive steak dinners.

“I work at a pretty high end steak house,” wrote server tjm003. “I got sat with a table of two and when I greeted them, I assumed they were a couple. It took them quite a while to order their food—I had to go back quite a few times and ask if they were ready.”

“After an hour of them talking…and looking at the menu, they finally ordered. The woman ordered a filet mignon and the guy ordered our most expensive steak.”


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

See where this is headed?

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


“She immediately broke down [and] said it was their first date and that they met on Tinder. Apparently she told him that a steakhouse was a little much for a first date and suggested coffee instead, but he said no.”

“As they were sitting there talking, he looked at his phone and said, ‘My daughter has an emergency,’ and he quickly got up and left. She was texting him after and he never replied. This girl bawled to me for 20 minutes, repeatedly saying, ‘What’s wrong with me?’”

“I had to reassure her he doesn’t know what he’s missing, blah blah. I went over to my manager and asked what we should do about the check. He said he was stuck, because it was a $250 tab and that’s too much to just not have her pay.”


“After a few minutes of convincing him, I got him to take everything off the bill. I boxed up all the food (including his steak and sides), brought it over to her and told her to enjoy her night. She stopped crying, thanked me, and left. After writing this I’m now wondering if they swindled me.”

That’s a pretty big commitment just for a free meal, but the writer does have a point. It could very well have been a scam.

It’s good to talk about shared interests on a first date.

But you should probably make sure you both, you know, share those interests first. Here’s what we mean.

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

Now that the scene is set, let’s introduce the other character.

“A few moments later, the guy arrived carrying a large bag,” continued CaptainWisconsin. “It was immediately obvious this date was their first. Their conversation was lurching from forced to downright painful when he reached into the bag and pulled out an album containing…”

Wait for it…

“…his Pokemon card collection.”


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

Unfortunately, his date was not.

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

Well, you know what they say. You can’t catch ‘em all.

Someday, historians will look back on our era and ask how we could have inflicted these mating rituals on ourselves.

Here’s a simple story with just enough cringe to keep you in tonight.

“The dude was waiting in the parking lot, singing and playing guitar when she arrived,” wrote garbagethegarbage. “He was dressed very formally, except for his sandals.”


Okay, folks, this is all totally normal. Nothing out of the ordinary here. Nope.

“They ate and drank,” the Reddit user continued. “He got up and squeezed in next to her on her side of the booth. She was trapped. She looked mortified the whole time. The whole thing was completely cringe-worthy.”

You don’t even have to wait for the first date for the awkwardness to kick in.

Technically this next story isn’t about a date. It’s pre-date. It’s pre-date to a date that will never happen, at least not if there’s any justice in this world. But it’s also terrific, and you deserve nice things, so here you go:

“I was working [at a restaurant] when a 19-year-old male (the kind of guy who seemed like he would have had a rough time in high school but has since blossomed) approaches a woman of a similar age,” wrote Reddit user and apparent restaurant employee Flavourtown69.

“[He] walks up, puts his elbow on the bar beside her, [and says,] ‘So, whaddya reckon about the Foo Fighters?’”


Do not try this at home.

After all that, we’re ready for a date story that’s not completely horrible.

In fact, this next one is kind of sweet, if you can stick it out through the terrible awkwardness. It’s not the couple’s first date, but…well, you’ll see.

Oh, and for you non-restaurant people out there, a “two-top” is industry lingo for a table that seats two. Likewise, a “six-top” seats six, etcetera.

“I had a two-top in a small booth and across from them was a family of six,” wrote Reddit user thebolda. “The two-top was in their mid-40s, maybe 50.”


“I was delivering food to the six-top and I was being berated for not using legs with my big trays, so I grabbed a pair and headed off. When I was setting them down a stacked plate on my tray shifted to the side and the whole tray pitched toward the six-top. I panicked and tried to stop it from falling and it all went backwards off the tray.”

What happens next is every server’s worst nightmare (after getting stiffed on a large-ticket tip, of course).

“Unluckily, I didn’t hear a single plate shatter,” thebolda continued. “I turned around and the woman at the two-top had rib sauce on her face, mashed potatoes in her bust, and broccoli all over her lap.”

“I started with, ‘I’m so sorry ma’am. Please stand up and we’ll get you cleaned up.’ My six-top was forgotten at that moment. I pleaded with her to get up so we could clean her off. Someone produced a towel for me. I had two managers trying to help. She was so polite and insistent that it was nobody’s fault. Her husband finally said, ‘At least wipe the sauce off your face.’ And she laughed and got up.”


“Everything was comped on their ticket … It was the only tray I ever dropped, and they never made me use legs again.”

So far, this story’s painful, but it isn’t that interesting. The real value lies in the epilogue.

“They came back in and asked for me the next week,” the Reddit user continued. “The husband told me they were celebrating 30 years together that night. I felt horrible. Then he told me on their first date she made spaghetti and accidentally dumped it in his lap. He told her it was karma and they had a huge laugh, and a free meal.”

All’s well that ends well. Even terrible dates. Try to remember that during your next terrible first date. Either that, or be careful on your way out the bathroom window.

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