Dating can be very uncomfortable; the person might not be a good match, the venue might be terrible, or a whole other slew of issues.The only thing worse than being on an awkward date is having to witness one. Unfortunately for waiters and waitresses, they witness these basically on a daily basis.
Restaurant servers on Reddit share the most awkward dates they've ever seen. Content has been edited for clarity.
"It was a typical Friday night, and pretty busy in the kitchen. A server comes in and asked if I spoke Chinese, I said yes, and he told me to go talk to some guest at a table. I told him they will have to wait because we are in the middle of a dinner rush. About an hour later, things slows down a little, so I follow up with the server. He proceeded to point out the table of guests that needed help. So I walked out of the kitchen with the expectation of maybe translating the menu for them or something. When I got up to the table, I notice it was a white guy and an Asian girl. So I ask the gentlemen how I could help him. He then asked me to translate for him. It was at that point I realize they were on a first date.
The guy asked me to translate a few things for him, like how did you enjoy the dinner, did you enjoy the date so far and other small talk. And I would have to translate that to the girl, and then translate her response back to English for him. This went on for about five to ten minutes. Eventually, he asked me to ask the girl if she wanted to sleep with him. The girl asked him if he had a girlfriend (I had to stand there and translate this conversation). Eventually, the girl shot the guy down, and it got pretty awkward at that point; so I found an excuse to get back in the kitchen."
"A young couple was at my table, they were probably 16. The girl was way overdressed for Red Lobster and a movie but it was cute. He went to pay and his card was declined. I felt so horrible walking back to the table. He said there should be plenty in his bank account, and I asked if he had put gas in his car before the date. He said he filled up his truck, some gas stations here hold the amount twice on a debit card after a certain hour and it drops off the next day.
The poor kid was so embarrassed he had no idea what to do. My boss paid for his meal, my tip, and gave him money for the movie they were planning to go to. Kid came back in two days later with all the money to pay my boss back."
"I'm a hostess, and when we seat people, we have to talk about the specials happening that day. Anyway, two people come in and they don't appear to be a couple, both were very stern looking. I start giving my spiel about the drink specials, she cuts me off and says she won't be drinking tonight. The guy looks at her and asks why. She tells him she's pregnant. And let's keep in mind that I am right there in between them with no option to walk away, because I am still holding the menus.
Well he freaks out, quickly questioning her, and getting very angry, she starts yelling at him. A lot of tension is floating around, and in the midst of all this anger about being pregnant, I chime in and mention that we are also having a special on our baby back ribs. The moment after I realize what I just said, they are staring at me with their jaws dropped, I look them dead in the eye and walk away. I am not good in these types of situations."
"My friend, 'Alex' was on a blind date with a friend of a friend. Alex gets a table at a fairly fancy restaurant where his friend 'Steve' works at as a manager. He arrives first and she gets there about 15 minutes late. No big deal, they chat over drinks. At this point he doesn't think it's going super great, but doesn't think it's too awkward. At some point after they order their food, she excuses herself to the bathroom.
A minute or so after she leaves the table he gets a text on his phone. It's from his date. It says something along the lines of, 'I hate blind dates. This guy is a total loser. At least I'll get a few free meals out of him.'
Alex realizes that the text wasn't meant for him, but for his date's female friend also called Alex.
He gets up from the table, finds Steve in the back and tells him what happened, asks for his half of the order taken off of the ticket, and then leaves before she gets back to the table.
Alex's date comes back from the bathroom apparently unaware that she texted the wrong person. Due to some mix-up, the entire order still arrives at the table. Reportedly, she didn't wait for or even question Alex's absence before she began eating. In fact she finishes nearly all of her meal before asking her waiter where Alex had gone.
The waiter checks with his manager, Steve. Finds out about the situation and informs her Alex left while she was in the bathroom. Then he hands her the check.
The best part is that she didn't have enough money to cover the check. She had to call a friend to come down to the restaurant and pay for her meal. (Steve wasn't too keen on letting her slide on the bill)."
"I'm a server at Red Robin, and I once served a teenage couple probably around 17 or 18 (easily seniors in high school). They had obviously been dating for a while since they already knew what they wanted, and ordered for each other. The 'date night' seemed to go pretty well; they ordered their drinks, ordered an appetizer, then ordered their food. Only their drinks had come out yet when finally after holding hands for a long while the guy looks into the girl's eyes and apparently broke up with her. I had been standing from a distance keeping an eye on my tables when suddenly I see this happening, and watch the girl's face just turn from happiness to just absolute horror. Tears well up and she started banging her fists on the table screaming out at him that he's an awful person and what not.
Everyone in the restaurant can hear it and everything just stops. As she's becoming more and more volatile, he's trying to calm her down. I'm not sure what to do at this point. Even my manager had come out and looked at me as if we both didn't know how to handle this.
Finally, the guy yells, 'Fine. Fine, if you don't want to be civil, then I'll go.'
She begs him to stay, but he pulls himself away and beelines for the door. She doesn't follow him.
He passes me on the way to the door, stops, and walks back towards me. He hands me 50 dollars and says, 'You can already obviously see why I did what I did. I just apologize that you had to deal with this here and now. Take care of her, and make sure she's okay.'
He then leaves.
She sat for the next three hours, not crying, but just staring blankly into the wall. She ate both of their meals AND the tower of onion rings.
On another note, a lady pooped herself at my work once."
"A guy comes in alone, asks for a table for two. I seat him in the corner in a booth where it's quiet and secluded, he says his date should be here any minute. I get him the drink he ordered and a bunch of chips and salsa.
Twenty minutes later, he's on his second drink and he promises me she's going to be here soon. She just texted him and said she's on her way. I really don't care because it's really slow and I like this guy because he's super low-maintenance. I brought him out some queso to go with the chips he was eating alone.
An hour goes by. There were two instances of a single woman coming in saying she was meeting someone, and both of these women were directed to this guy, but neither of them were his date. Now I'm kinda feeling bad for the poor fella.
Three hours after I sat him down, he'd had nine drinks and I brought him a few rounds of shots occasionally just because we (the entire staff knew what was up by now) felt so bad for him. He was freaking hammered.
He goes out the back door to start puking in the alley, as his date finally walks through the door. I sat her down at their table, got her drink, then went out back to give the guy a smoke and let him know his date was here. He was not happy.
I walked him back inside, sat him down, and watched them formally introduce each other. I did not realize this was a blind date. I left awkwardly and immediately.
They paid and left maybe five minutes after that, just enough for the lady to finish her drink. I guess she gave him a ride home, but I don't really know. I didn't think she was actually going to show, otherwise I'd have cut him off well before that.
Oh well. Hope he got laid that night."
"I was working at a cafe for a while, I've seen a few awkward dates happen. One comes to mind in particular.
Guy and girl come in and take a seat, order food, the usual. The date seemed to go generally well until it came to paying for the bill. The girl, all of a sudden, starts kicking up a fuss about the food they'd just eaten. She was pretty loud. My co-worker was very apologetic about it all, offered to give them a discount. The girl made a huge deal of getting the entire meal for free, saying she was a law student, blah blah blah.
The guy is looking clearly embarrassed and offers to pay for the meal, and not to worry about it. The girl snaps at him, tells him not to pay for bad food/bad service and storms out. Co-worker gives the guy a discount and he pays for the lot. Guy tells us that it was a blind date, they'd met on OkCupid."
"I worked in a bar while I was in college, and I had a guy come in before his date. He told me that whenever he ordered a certain drink, what he really wanted was Chardonnay. I must have given him a weird look, because then he got embarrassed and confided in me he was really in love with the woman meeting him there for the date. He told me how she usually dated guys that were more macho, and he didn't want to order Chardonnay in front of her. If he ordered anything else, he would make a face because he didn't like the taste. I felt pretty bad for the guy so I agreed. He seemed like a genuinely nice man and I wanted to help him out. Well the woman this nice man was in love with was a total brat. She came in with two other women to their date, he mumbled something to me about maybe not being clear, and plastered a smile on his face.
The woman was extremely charismatic; she was one of those 'life of the party' women and the guy was very quiet. Later in the evening he ordered another drink like he had been doing this all night. Only this time when I brought it to the table, she insisted she wanted to try it. She said that she had never had the drink before, and wanted to try it.
It was like watching a train wreck, he tried to stop her saying things like 'Here, let me buy you a glass.'
Well she took one sip and knew it was Chardonnay. I tried to help him going over and apologizing pretending it was my mistake, but she guessed the truth and started teasing him. Her friends joined in laughing as well. I felt awful, and I could tell he was really embarrassed, even though he was laughing along. After a while he asked for the bill, I brought him the tab with his and the woman's portion and he told me he was paying for everyone. I felt so awful, the woman and her friends had all had so many drinks the tap was over 100 dollars, but I brought it and he tipped me 50 making me feel if possible more awful.
They were my last table so I closed out with my manager, and went back into the bar to have a drink with another girl that worked there. The group was still there so I decided to go over and ask to buy him a drink. I just wanted to, I don't know help him or something. Make him look good and possibly make that woman jealous. Well I went over there and asked if I could buy him a drink. He smiled at me, got up from his chair, and took me aside. He told me I was very beautiful, but I was too young to be hitting on men old enough to be my father. I almost explained to him that I was just trying to help him, but decided not to. I figured that he could use the ego boost after that 'date.'"
"For a couple summers during college, I waited tables at this really nice Italian place. A guy sits down in my section and says he's waiting for his blind date. I immediately feel sorry for the girl before I've even seen her, because this guy doesn't look the nicest. Way too much gel in his hair, smells like he bathed in cologne and constantly talking on his Bluetooth with co-workers.
The girl arrives and she's nice enough, but I can tell the date isn't going to go well. He tries to order for her and she's having none of that. He starts talking about a recent business trip he went on with some co-workers. She is utterly unimpressed and continues reading the menu. It's clear he's getting impatient, so he starts listing some of the dishes to try and get her to order faster. He clearly had no idea what he was talking about because he was totally butchering the names.
Finally, they're ready to order and the guy snaps his fingers at me. I go over and ask what they want. He orders some pasta, once again completely butchering the pronunciation. The girl turns to me and orders her meal in fluent Italian. I nearly drop my pen. The guy goes white as a sheet.
She gives him this smile and says 'Oh yeah, I'm pretty much half Italian, so I've known all about this stuff since I was five.'
I had to try very hard not to burst out laughing. After that, it was clear which of them had the upper hand and, needless to say, they did not come back."
"I had a woman come in alone and ask for a table for two on a very slow weeknight (unbeknownst to me, this was my last table of the night). She told me it was a first date and was very nervous. She jokingly asked me not to judge her for how quickly she drank her first glass. Fifteen minutes passed, and I started to feel bad for her. She took turns glancing at her watch, her phone, and the door. Thirty more minutes and another two glasses later, I politely informed her that the restaurant would be closing in half an hour. She looked worried and immediately pulled out her phone and began typing furiously.
Ten minutes passed until she excitedly exclaimed, 'He's five minutes away!'
Ten minutes later, he waltzed in the door, threw his coat on the booth, and exclaimed, 'I gotta pee real quick.' He returned from the bathroom and dismissively told me he'd have a Coors Lite bottle when I approached the table to ask him what he'd like to drink. When I showed him the drink list sitting in front of him and informed him we didn't have Coors Lite or any bottled drink for that matter, he ordered a Bud Light bottle without looking at the list or bothering with such trivial things as eye contact, manners, or listening. Sigh
Once I pointed out the drink list for the second time, he chose a drink that we did have and then launched into a monologue without touching his food menu. I quickly returned with his drink and asked if he was ready.
'Hey, I just got here! Can I get a minute?!' He snapped.
I walked away before I punched his ear off and went straight to the kitchen to relay his message. They kicked me back out through the still swinging door with a message of their own for this man. I returned to the table with a much more polite version of 'order now or the kitchen will find out where you live and splooge on everything you hold dear.' Needless to say, he had a billion questions about every item on the menu, and ended up ordering the most time consuming and complicated dish to prepare that we had. Also the most expensive. I dashed to put the order in at 8:59 pm (we close at 9).
At the end of the meal (now 11 pm), I finally had enough of being brushed off and firmly dropped the check between them, insisting that they at least pay so I can go home. They were told that they could certainly stay and order drinks through the bar, but I had class early the next morning and could not stay any later. Prince Charming excused himself to the bathroom and stayed there for an exceptional length of time (seemingly to avoid paying) so this poor woman ended up throwing her card down for the bill. She left me a handsome tip and I left immediately after finishing my money. No idea how the date ended but I seriously hope he didn't get a second date."
"A guy from my country's 'As seen on TV' commercials in the 90's, and a rather pretty younger lady were on a date. He was about 15 years her senior, if not 20, and she was way out of his league in the appearances department. Well-dressed in a nice black dress, elegant jewelry, perfect makeup that made her look like she was born that way, perfect posture, nicely done hair that looked fresh from a conditioner ad. He on the other hand looked very much like John C.Reilly with worse hair, a kind of crack-head look in his eyes, a tweed jacket, and mismatched blue dress pants.
He was talking like he was in one of his commercials, raving about his house, his pool, his spa, his jaguar, all the while topping up her drink that she was silently sipping on every ten seconds or so. They nailed the first bottle in about an hour, mostly her I imagine, then by the time they were three quarters through their main meal, she was plastered, and ran to the bathroom to throw up. He was left sitting at the table (unable to join her in the women's bathroom), looking awkward and with the whole restaurant whispering about the scene that had been playing for the past two hours. It was in the paper as a side note of the celebrity gossip column the next day. I felt bad for both of them."
"I remember serving this one couple who had just come into the restaurant. They were like my second to last, or third to last table. I don't really remember.
What I do remember is I of course introduced myself, and I started to them about the food, and asked what they were doing here, all the while the guy just straight up glares at me the whole time. The girl, on the other hand, was asking me questions, and chatting it up with me. She was cool. I told them I was saving money for my wedding that is coming up, and she kept asking me questions about her and we got into the conversation of love and stuff. I put their food in, get their drinks, and we start talking again. This time, we talk about my wife again.
But, the guy says to me 'You know, instead of serving us, why don't you sit down and entertain us. You seem to be doing a better job then I am.'
I didn't think about what he said at first, casually joking that I am just doing my job and the like. He pays for the check, leaves a bad tip. The girl comes to me and was like, 'I am so sorry about him, tonight is our first night and he was really jealous of you.'
I looked at her incredulously and said 'I was talking about my fiancé the whole time.'
She said 'I know. Did he leave you enough tip? Here, here is some more."
She left me a bit more on top, and as they were walking out the guy just glares at me.
That's the most awkward first date I have ever seen."
"I worked at a Chart House. It's kind of ritzy, and we'd get a lot of high profile people/events. One of the big things that we (the servers) all loved was proposals. I worked there for a year and a half, and I probably saw twenty of them at least.
So what would happen is the server (if they knew beforehand) would tell everyone, and we'd keep trying to peek over or generally be around that table when they were finishing up. It's always at dessert time that the dude will go for it. It's such a neat thing to see, and always made us feel really good. So anyways, that's the setup for the incident I'm about to describe. We had an electrician who handled all our lights. Cool guy.
We had a crazy lighting setup, and he handled everything so the place always looked real nice. Anyways, a couple hours before work one day I hear him palling around with my GM and floor manager in the office. I go in to ask for a set of keys I need to operate the elevator, and pick up enough of their conversation to realize that he's bringing his girl in later to propose. He's hoping they do something special for him. Make it really cool, you know. Special. I do the elevator thing, dump the boxes I was getting behind the bar, and then ask my GM what the game plan for the proposal was.
GM says they're gonna make him our signature lava cake, but really dress the thing up. We had a head chef who could cut a lemon into a little mouse, all kinds of cool things. He made an owl out of a pineapple once. True works of art. So this cake looked amazing. Like, it was seriously amazing. He spent a good bit of time layering it up all cool. For a bunch of jaded servers, we were all genuinely impressed when we saw what he did with that cake. This electrician was getting the works.
So we're all doing our normal pre-proposal thing, which is sort of hovering around as best we can in the hopes of catching the big moment. We learn that their server, Lauren, has been given the ring in advance and will be dropping the (impressive) dessert to the center of the table, before nonchalantly placing the box alongside it. We were puzzled by this, but figured he had a plan.
His plan was to stare at the ring box. He just stared at it. Then she stared at it. Then she looked at the dessert, looked at the box, and then looked back. All twenty of us were crowded around in the bar lounge, peering through the crystal divider that separated restaurant from bar.
Hushed whispers 'Is he gonna go on one knee?' 'What's he saying to her?' 'Oh my god! Oh my god! Oh... oh no,' 'She looks mad' 'Oh no, I can't believe Larry's getting shot down!' He said a few things to her that we couldn't hear. It was surreal. She never touched the ring, either. Just sort of sat there, seething at this incredible dessert that was now starting to fall apart. We were mortified, and a moment later she suddenly got up from the table and walked off. Larry went right after her, but like trailed five feet behind. Just following her, dejected.
I'm pretty sure he quit after that because we didn't ever really see him again."