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I used to wait tables, and let me tell you... I saw some weird things on the job. Mostly entertaining things, actually, but ocassionally awkward things. Like bad first dates. I once had the unfortunate experience of seeing the most awkward first date between two people who seemed unable to start a conversation. Every time one of them would try, the other would look down or look away. One trembled noticeably. I think they were both nervous and anxious people. They tipped well, for what it's worth, and I do hope they figured something out.

After Redditor Flavor_Town asked the online community, "Waiters and Waitresses of Reddit, what's the most awkward first date you had to witness firsthand?" people shared their stories.


"This one time..."

I worked at a bar where like 50% of our business was from Tinder dates.

This one time, two guys came in separately and sat at different tables by themselves, along the same wall. They were both facing the door and clearly waiting for dates.

Eventually, a woman comes in, walks up to the closest guy, sits down and they start chatting. They start ordering drinks. After ~5 minutes, the other guy, who is still waiting by himself, gets up and walks over to the couple. He says 'hi' to the girl and is like 'um aren't you so-and-so? ...I'm so-and-so we were supposed to be meeting?' She was clearly flustered, lots of awkward laughter, and she gets up and goes with the other guy to the other table.

A couple of minutes later the other woman shows up and sits with the first guy and he tells her all about it.

franklylove​

Okay, that was really cute.

Truly.

But it gets worse from here.

Let's continue.

"Painful to watch."

Once, as a high school teenager, while waiting tables at a now-defunct Mexican restaurant chain (think Applebee's, but tacos), a first date came in. They seemed unable to converse. It was super awkward. Painful to watch. Well, at one point the woman asked for a refill of her tea. I dutifully went and got the pitcher and came back to fill her glass. While pouring, i literally dropped the entire pitcher, a full gallon, of sweet, sticky tea directly onto her. It went down her shirt. Her skirt. It was everywhere. She was completely and utterly soaked. My newly blossoming career as a server flashed before my incredibly stoned eyes. I apologized profusely. I brought her out like 4000 napkins. Her date was dumbfounded and probably thinking "didn't think this could get worse, but here we are".

Well, she cleaned up the best she could. And they ate their meals. And, magically, they began talking. They started looking at each other as a new couple looks at each other. They laughed. They enjoyed their s*** food. She dried out.

They left the restaurant an hour later, with her arm in his. They gave me the biggest tip I had ever gotten. I got $20 on a $20 bill, in 1996.

Somehow, my idiotic, high blunder, turned the worst first date ever into the best first date ever.

I like to imagine them now as happily married, parents of 7 lovely children, who love telling the story of the moron who poured an entire gallon of tea on her, 25 years ago.

AmishTechno

Let's hope they married...

...because I cringed reading that!

Let's continue.

"Whole time they're sitting at the end of the bar..."

Worked at a pub connected to a brewery in college. Dude comes in with a stunning woman, I mean she's absolutely gorgeous. Whole time they're sitting at the end of the bar, and you can hear the guy talking about how he has a room for them next door at the hotel in downtown. So they decide to go to the brewery next door, gonna pull a little dine and dash. They got over there and didn't realize we are on the same system, so he orders a couple of beers, and the bartender on the brewery side asks if he wants to add it to his tab. He looks over confused and says "what tab? I've never been here." She prints off the restaurant bill plus his brewery tab, it's like $80 or so. He just blankly stares at the poor bartender, flies off the handle. The girl he was with ended up paying for it. They walked across the street and to the hotel, he has already invited her up, she stalls until her Uber gets there and then just dipped out. Kinda funny, kinda awkward, but that's what you get for dine and dash.

stocky_stegosaurus

"I head over to take their order..."

I used to work at a Mexican restaurant and one year when I was working on Valentine's I was subject to one of the weirdest first dates ever.

A couple walks in, she is dressed to the nines, like she's ready to hit up a club. He is dressed more casually, in jeans and a button-down. Our hostess seats them and when I go to greet them the man announces that this is their very first date! The lady looks less than impressed and gives a small smile, more like a grimace. They order drinks and as I'm watching their table you can tell that the date is not going well. The guy is talking animatedly and the girl is glancing around like she'd rather be anywhere else.

I head over to take their order and it's clear that I've interrupted something. The guy looks a little embarrassed and sad and the girl looks pissed off. He orders his meal and she flippantly orders something (seafood enchiladas) without really looking at the menu. She tosses her menu in my direction and sucks down the rest of her drink. Okaaaaay then.

I deliver their food and go back behind the counter to continue rolling silverware and watching my tables. They dig in and the man seems to be enjoying his food, his date looks disgusted and is flicking bits of her dinner around the table/floor. I walk over to check in and see if she maybe wants to order something else. I get to the table to ask how everything is and she gets up, SCREAMS that her food is DISGUSTING, and goes OFF about how s**** this date was. She started yelling at him about how he should have ordered for her, how dare he take her to such a low-class place, she was so done with this, blah blah blah. She shoves her plate away, gets up, and storms out of the restaurant. The dude is mortified. I tell him I'll be right back with the bill and would he like his food boxed up? This guy shakes his head, pulls her plate towards him, and says nope, he's fine to continue eating the meals he's paid for.

He stayed for the duration of his meal. I never did find out what happened to the lady. We talked about that incident for WEEKS after!

TheTrickyBullet

"A couple was shown to their table..."

A couple was shown to their table, and the guy was on the phone the entire time. I normally wait until guests are off their phones to give my spiel, the specials, and such and take a drink order, but he didn't show any sign of getting off the phone. I take the order, which the guy just holds his hand over the phone, talks over his date. When I come back, she attempts to order an app, our house specialty, and he tries to say the portions are large enough without. She orders the zucchini anyway. I get the dinner order, and bring out the app. At this point, I hadn't been to the table when he hadn't been on the phone. While I was putting together the salad, the woman comes out to the lobby and asks to get her meal packed up. She ended up paying her half of the bill and ducking out. She told me this was their first date and she was set up by a soon-to-be-former friend. Said she was going to be calling her friend as she walked out. When I brought the guy's meal to him, he asked where her dinner was and I told him what happened. He really thought she was in the bathroom...

newguy1787

"Then she leaves..."

Not a first date, but very awkward: a guy comes in with an escort and drops a good amount of money on booze at the bar. Then she leaves a few hours later, and he informs us that his wife is on her way to meet him for dinner and tips us an extra $200 to keep our mouths shut. Keeping it classy!

InelPalmisano​

"A teenage couple..."

A teenage couple sharing an ice cream and holding hands very awkwardly. After they finished the ice cream they kept talking about their - very adventurous - sexual fantasies. They were around 14 years old. Super awkward to have to interrupt them to ask if they want anything else.

Ashley_42

Wow.

They grow up so fast, don't they?

Bet they were loud in the way teenagers always are, too.

Let's continue.

"I used to work at a sushi restaurant..."

I used to work at a sushi restaurant in Anchorage, and there was a girl who would come about once every few weeks with a different guy. Every single time, she ordered a heodubbap, which is like a rice-salad-sashimi bowl, and it was GIANT. I've only ever seen a handful of people ever finish the entire thing in one sitting. She would finish the whole thing (with CHOPSTICKS) and always ask for a spoon towards the end. It was always fun watching the guys look stunned when she finished.

One day she came with this dude that ordered what she did, and when they both finished the bowl, they ordered another and split it.

Wish they had ended up together but she came back with a different guy a couple weeks later.

themerrypanek

"One time a person..."

I worked as a barista at a coffee shop with a dishwashing sink that brought you face to face with whoever was sitting at the coffee bar across from you. For some reason, so many people chose this spot for their first dates, so I would have to wash dishes and pretend I wasn't literally on the date with them.

One time a person I knew was on their first date with someone and chose that cursed seat across for the dishwashing sink. Because we knew each other, we chatted a little bit and then as if a partition raised between us, they began their date... but I still had dishes to do..... So uncomfortable.

maybemaggot

"After the appetizers..."

I had these two people that were there on a first date. After the appetizers, this poor man got the s**** and was going back and forth to the bathroom all night. There were only a few other people in the restaurant at the time so it was noticeable and they were chuckling every time he got up. I honestly felt so bad for the guy.

RAM592

I'll close this out...

...with another story.

Some years ago I waited on a man who kept barking at the staff when his date didn't show up as planned. It was awkward to see him getting more visibly upset as time went on. I later ran into his date... who'd been sitting at the bar eating onion rings and tossing back a beer the whole time and had decided when she walked in that she didn't find the man attractive but didn't have the heart to say anything about it.

Ouch.

Have your own stories to share? Feel free to sound off in the comments below.

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