Everyone has been on an awkward first date, but imagine what it's like for the server. Waiters, waitresses and bartenders alike look back and share their horror stories of the most awkward dates they've had to deal with.
“She Was Already A Little Tipsy”
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“I had a table once where this guy came in for a blind date. When the girl got there, it was obvious she was already a little tipsy. Well, a little ways into the meal and after having one drink, she threw up all over herself at the table. She went to the bathroom and the guy had to ask another server to go check on her. In the bathroom she also proceeded to vomit all over the toilet seat. I felt so bad for the guy, but he was so nice about it. He waited for her to get cleaned up and took her home. That must have been the most awkward car ride ever.”
“She Leaves The Table, He Gets A Text On His Phone…”
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“This happened to a friend of mine. ‘Alex’ -not his real name but it works for this scenario as unisex first names end up being important.
He’s on a blind date with a friend of a friend. Alex gets a table at a fairly fancy restaurant that 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, 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 that 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).”
Blind Date From Hell
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“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 that 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 was 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 out of it.
He goes out the back door to start puking in the alley, as his date finally walks through the door. She looked like she had just been crying her eyes out and she seemed incredibly flustered. I didn’t want to pry, especially considering the mess she was about to have to deal with. 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, but oh well, I hope he got laid that night.”
“A Couple Walk In And The Lady Sitting By Herself Goes As White As A Ghost”
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“I was a bartender for a number of years, but one story, man, this stands out.
This younger lady comes in by herself, comes up to the bar, and says she’d like a table in the back, alone. It’s a slow night, I was working alone, so I sat her, brought her a drink, etc. She’s there for about an hour, has a couple of drinks, and keeps checking her phone. I finally asked her if she was expecting someone, and her response was a sad smile and a nod.
Almost immediately after that, this guy, early 30’s comes in, asks for a table for 2. This guy reeks of sleaze. On his arm is this slightly trashy, very early 20’s girl who’s already out of it, loud, and freaking obnoxious. She keeps talking about how lucky she is to finally get this guy out with her, how it’s been the best first date ever. I get them their food order, and they can barely keep their hands off of each other. I also noticed that the lady sitting by herself has gone white as a ghost, and is shaking a little bit. She takes out her cell phone and takes a few pictures.
Around this point I know what’s going on, and I just try to avoid it. Lady number one walks up, puts some papers down on the table, and says, ‘We’re getting divorced.’ She then looks at the lady, who turns out to be her little sister, and tells her to never talk to her again. She then comes up, pays for her meal, and walks out, leaving the most utterly destroyed first date I have ever seen. It was phenomenal. I got a few more of the details when she came back later: this was not the first time he had cheated, just his first time with the sister.”
“I Notice There Is A Girl Having A Drink With My Date”
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“I was working at a restaurant, and this guy I had met a few days before came in before my shift ended to wait for me, he was going to take me out as soon as I finished. He was a few hours early, I brought him a drink and told him it would be a while, and he said that was fine. The place got pretty busy and after a while I notice there is a girl sitting down with him having a drink. I went over to bring him another drink, he introduced her as an old friend from school, and she kind of just gave me a quick up and down, seemed annoyed, and started chatting away with him, giggling at everything he said, it was a bit weird to watch.
My boss asked me if I could stay late because it had become so busy, but I said no, I’m actually going on a date and pointed him out. She laughed and said, ‘Really, with that guy that’s been drinking with that other girl?’ I sheepishly said yes. The girl had left just before I was done, but he was pretty out of it by then. I asked him if he still wanted to go, and he said of course, but he ended up being so messed up, that I left and went home. I went out with him some other time, and again he got way too out of it and passed out. I turned him down the next time he asked.
About a year later, I was working at a different bar and he and the girl he was talking to at the bar on what was supposed to be our first date walk in as newlyweds. I found this out when she told the bartender she wanted to beat me up or something because I was trying to ‘take her man.’ So yeah, that was pretty much the most awkward first date I have seen while working as a waitress, and it was mine.”
“I’m Not Supposed To Do This But…”
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“This one starts out awkward but takes a bit of a turn. I’m a host. I sat a gentleman, very well dressed, named Greg who told me he was meeting a girl for their first date. About half an hour passes, and no one shows up. It’s a Sunday night so it’s pretty slow, so I come by and check on him. He hasn’t heard from her or anything. Another half hour, then another. He finishes his entree, pays, and walks up to me and says, ‘Man, she’s not coming. Whatever.’ I try and convince him to stick it out at the bar for a little bit but he isn’t having it. He leaves. 20 minutes later, a girl shows up. She says her phone is dead and her car broke down on the way to her date with a guy named Greg. I say he got fed up and left and she starts to cry because she really thinks she messed up. I tell her it’ll be okay. The guy signed up for a rewards program and we had his cell number. OFFICIALLY I’m not supposed to do this but I called him up and told him his date was here, and he didn’t believe me, so I put her on the phone and he was back 20 minutes later. They seemed to really hit it off, and as he left he said ‘Thanks man’ and slipped me a 5 (the only direct tip I’ve ever gotten). They just came in together yesterday. It makes me really happy that they’re still dating.”
“I Had A Guy Come In Before His Date And Tell Me…”
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“I worked in a bar while I was in college and I had a guy come in before his date and tell me that whenever he ordered a scotch what he really wanted was chardonnay. I must have given him an off look because then he got embarrassed and confided in me that 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 wine in front of her, but 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 witch. 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. Anyway, later in the evening he ordered another ‘scotch,’ 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 scotch before. It was like watching a train wreck, he tried to stop her, saying things like, ‘Here let me buy you a glass’ etc. Well, she took one sip and knew it was wine. I tried to help him by 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.'”
“The Poor Kid Was So Embarrassed”
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“A young couple was at my table, they were probably 16. She 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 2 days later with all the money to pay my boss back.”
“When I Come Over She Was Eyeing Me Like A Ribeye Steak”
“Here’s the scene-Chain Restaurant, the lucky guy, must have been in his 50s, skinny, black, wearing loudish clothes and talked in (I kid you not) constant ’70s jive, like:
‘Hey, folks, I’m David, I’ll be taking care of you.’
‘Right on, mack.’
‘Right. So, would you like to start off with some long island ice teas?’
‘Yeah, brotha, we’ll get this started right and funky-get this queen a margarita, while I’m digging on that long island special.’
It goes from there.
The lucky girl: curvy, likely 30 or less, black woman who from the moment they sat down seemed bored with his crap.
When I come over (I’m black with dreads-and ladies love the dreads), she was eyeing me like a ribeye steak.
I go do my thing, come back, he’s in the bathroom and the trash talking commences:
‘I can not believe I’m on a date with this clown. I’m sorry about the way he talks, I didn’t know from the (whatever online dating site). Anyway, how old are you? Can I touch your dreads? When do you get off?’
So I take their food order, tell my friends about his ridiculous ’70s act, have one of them bring their food out when it’s ready and my friend comes back, like ‘I think you need to go to your table.’
She’s on her cell phone, bored, he’s looking angry, asks me for two boxes and the check. I box their stuff, bring it back, he pays the check, takes off stiff-legged and she breaks out into a smile, asks for a plate, unboxes her meal and eats, continuing to flirt with me until leaving.
The guy was kind of clownish, yeah, but the way she did him was painful.”
“When I Come Back They Are Now Sitting Next To Each Other And She Is…”
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“Young couple came into my restaurant, probably college aged because I feel like high school kids don’t go on blind dates. I was managing/bartending that night. The kid comes up to my bar and asks for two Miller Lites, I said ‘1) I need your ID and 2) We don’t serve Miller Lite here.’ ‘What do you have that’s similar?’ Sarcastically, I tell him ‘The goose Island IPA is indistinguishable from Miller Light.’ ‘Let me get two of those.’ ‘No.’ ‘Why not?’ ‘I just saw you shuffle between your real ID and this bad fake.’ He walks back to the table mumbling swear words, and explains to his date that we don’t serve the champagne of beers. A couple minutes pass and they’re flirting with each other from across the table. I go downstairs to change out a keg and when I come back I see they are now sitting next to each other and she is giving him a handy with the same ferocity the Hunchback used to ring the bells of Notre Dame. I yelled at them to get the heck out and the dude said ‘hold on,’ so I pushed him out of my restaurant, pants around his ankles.”
“He Asked Me To Translate And Ask The Girl…”
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“I wasn’t a server, but I was a line cook at a restaurant. 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 slow 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 5-10 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.”
“If Looks Could Kill, I Would Have Died That Night”
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“I worked at a smoke lounge a few years back, and my husband would come in all the time. One night, it was packed, so a couple invited him to sit with them. It turns out they were on their first date, which wasn’t going very well for the gentleman because this girl sat there for 5 hours trying very hard to get my husband to leave with her. After closing, she waited outside for him, followed us to our car, and gave him her number. He, being the mean person he is (I love him dearly) called this girl and asked if she wanted to go on a double date. She shows up, expecting to be on a date with him and his buddies. She asks me when my date will get there, to which I reply my husband is my date. If looks could kill, I would have died that night. And she STILL tried to get him to leave with her.”
“I Seriously Hope He Didn’t Get A Second Date”
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“Thought this lady was going to be stood up, and everyone (including her, I hope) really wished she had been.
Had a woman come in alone and ask for a table for two on a very slow weeknight. 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. 15 minutes passed and I started to feel bad for her. She took turns glancing at her watch, her phone, and the door. 30 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. 10 minutes passed until she excitedly exclaimed, ‘He’s 5 minutes away!’ 10 minutes later, he waltzed in the door, threw his coat on the booth, and exclaimed, ‘I gotta pee real quick.’ (If you’re keeping track, I had 10 more minutes until the kitchen staff either stabbed me, burned the place down, or went home). He returned from the bathroom and dismissively told me he’d have a Coors Lite bottle. When I showed him the drink list sitting in front of him and informed him we didn’t have Coors Lite or any bottle 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 list for the second time, he chose a bottle 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?!’ I walked away before I ripped 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 (there were some colorful phrases and words sprinkled in there). I returned to the table with a much more polite version of ‘order now or the kitchen will find out where you live and go after 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.”
“The Girl And I Start Talking Again But The Guy Says To Me…”
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“Oh god, I remember serving this one couple who had just come into the restaurant.
I introduced myself, and I started to tell 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 my fiancée and we got into the conversation of love and stuff. I put their food in, get their drinks, and we start talking about my fiance again. 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 than 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 fiancée 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.”
“I Was Rooting For Him Because I was Nerdy Too”
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“I worked as a barista and witnessed numerous obvious first dates. One time this super nerdy guy brings in this pretty attractive girl. I’m rooting for him because I used to be quite nerdy and had a tough time with the ladies. Anyway, the guy starts talking on and on about his favorite sci-fi/fantasy books as well as some card game that sounded similar to Dungeons & Dragons.
There’s nothing wrong with those interests, but the girl was clearly not receptive. She was giving him all kinds of physical and verbal cues that she wanted to change the discussion, but this guy would not stop talking. While I was watching, I wanted to help him, tell him to change the subject or something, but I couldn’t think of a smooth enough way to help out.
Maybe it was because he was nervous, but when he gets up to go to the bathroom, he knocks the table which causes the girl’s hot latte to be spilled all over her. He apologized profusely but you could see she had checked out of the date. She left after drying herself. Hope he found a girl that appreciates sci-fi books and Piers Anthony as much as he does.”
“It Was In The Paper The Next Day”
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“It was a guy from ‘As seen on TV’ commercials in the ’90, and a rather pretty, younger lady. 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 speed-freak 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, etc. 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 Once Served A Very Interesting Table…”
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“I don’t know if this was a first date, but I once served a very… interesting… table that has stuck with me.
The man was white, with a white tank top on, long hair, goatee, and probably hadn’t showered in a while (he stank and looked like he fell in oil). The woman was black, very tall, with wonderful hair that that curled in every direction. Long, fake, neon nails and a lot of cleavage. They ordered wings and a pizza. No problem. As I deliver the wings to the table, the woman turns to the man and says, ‘You wanna get that pizza to go?’ The guy nods and says, ‘Yep, we got plenty of protection back at the hotel, let’s get out of here.’ I grabbed their check for them, had the cooks box up their pizza, and got them out. I should mention that the guy kept giving me the ol’ up and down and licking his lips every time I spoke with him.”
“It Seemed Almost Like A Perfect Moment Until…”
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“I’m friends with a dude that bartends at a hotel bar. I was sitting at the bar, talking with him and my girlfriend one night.
This girl sitting near us is a regular at the hotel, but lives out of town. We talk to her for a bit, and before long, this dude, also an out of town hotel regular sits next to the girl. They start talking.
My girlfriend and I listen in on the conversation-it seemed almost like a perfect moment from that movie ‘Up in the Air,’ where two frequent travelers hit it off.
Their conversation keeps going, and things are looking okay until the girl starts talking about Doctor Who. Like, really, really, really talking about Doctor Who. The guy was unfamiliar, and wasn’t too into it, but it didn’t matter, this girl was going to make him a fan. She started showing him clips. You could see him getting less and less interested, but his food had shown up and there was no way to extricate himself from the situation. As soon as he was done eating, he found a reason to go back to his room.”
“She Tells Him…”
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“I’m a hostess and when we seat people we have to talk about the specials happening that day. Well anywho 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…”
