Ruin My Week
Ahh, awkward first dates. We never thought we’d miss you but this past year has taught us that we can crave even the strangest of human interactions.
The people of Reddit are talking about some of the most awkward first dates witnessed by a most reliable source: restaurant wait staff.
Who else gets a front-row seat to some of the most awkward of awkward situations between two people?
Get a strong dose of second-hand embarrassment with these 31 extremely awkward first date stories.
1.
“I had these two people that were there on a first date. After the appetizers this poor man got the shits and was going back and forth to the bathroom all night. There was 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.” –RAM_592
2.
“At a restaurant i worked at, there was a white guy and a black guy on a first date. They were sitting in a booth and having a good time. White guy gets up to go to the bathroom. When he came back he sat in the wrong booth with a different black guy. Took him a minute to realize it was a different person. The person he was on a date with was not happy at all. They tried to salvage the date, but it didn’t work.” –Bluegunder
3.
“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. Couple minutes later the other woman shows up and sits with first guy and he tells her all about it.” –frankylovee
4.
“Lady comes in to get a table says she’s expecting a man and gives us a brief description. He shows up about 10 minutes later and she starts saying she knew it, he looks very surprised and scared. I took a drink order and when I get back they are gone. The hostess fills me in that in my absence they had a heated but civil exchange, the man was married to the lady’s cousin also the lady was married. Apparently they had been texting for a while after meeting via Craigslist personals. I’m assuming the married but looking section. Don’t known if they hooked up in the end or just called the whole thing off.” –Hazmatt40oz
5.
“Not a first date, but very awkward: 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!” –InellPalmisano
6.
“I was working at a high end steakhouse when a couple comes in on a first date. The man was really friendly and seemed like he knew his wine. He orders a nice and fairly expensive bottle. As I’m presenting the bottle, the woman’s phone rings and she answers. Apparently, her close friend just broke up with her boyfriend and is distraught. The woman asks if her friend can join them for dinner. The man says “of course” and is really gracious about the whole thing. The friend shows up within a few minutes and is a crying, hot mess. I bring the friend an empty glass and before I can pour it, the first woman grabs the bottle and fills the glass to the brim, then requests another bottle. After I open the second bottle, the man excuses himself to the restroom. While he is away, I overhear the friend expressing concern about the menu prices. The first woman then says “Get whatever you want, I’m not going to ever see this loser again.” So then I catch the man coming out of the bathroom and tell him what I just heard. He says “What do I do?” I tell him he is welcome to leave through the delivery door in the back and I will play dumb for his date. The guy expresses his gratitude and slips me $100 on his way out. The woman becomes increasingly irate as the night goes on and she realizes the man isn’t coming back to buy them food. She waits until closing time before settling the alcohol tab and leaving hungry in a taxi.” –kelpat14
7.
“Just saw one on Valentine’s Day. The date seemed to be going very well, actually, not awkward at all. They talked non-stop, no lulls in conversation, they were laughing, carrying on, and just generally having a good time. In fact another server and I were laughing about how obnoxiously loud they were. Then I heard the gentleman say “…and obviously you’re not still married… right? Please tell me you’re not still married,” she said “well, actually…” and then things got VERY uncomfortable. It must not have been a deal breaker because they stayed at the restaurant another hour until we closed, but they were very quiet for the rest of the night. Hardly spoke to each other at all.” –WhatOnceWas396
8.
“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
9.
“Not a first date but we did have a guy come into our steakhouse on a Saturday night at 7 pm with NO RESERVATION. He then told us on the spot he was going to propose to his girlfriend. We had to seat them somewhere awful, it was right next to the bathroom and when he got down on one knee, looking around nervously, absolutely no one noticed. Him and his gf kept waiting for the rest of the restaurant to see them and go quiet or even clap for them but not a single person noticed. She said yes, looked disappointed and they went back to dinner like nothing happened. They must not have minded too much because they came back for their one year anniversary, this time he made a reservation!” –sophiegitt
10.
“At the end of the dinner, 2 couples on a double date dine and dash. I chased them down, and the girls had no clue, their dates had told them they already paid. The girls ended paying, the guys had no cash.” –joellyy
