Perhaps there is nothing more cringe-worthy than witnessing an awkward date in the wild. People don't go into dates expecting them to be awful, but when they are, the only thing to do is just endure it until it's over. Some dates are so bad they make not only the parties involved uncomfortable, but everyone around them too. The secondhand embarrassment is real. These Redditors shared the more cringe-inducing dates they ever had the displeasure of witnessing. Content has been edited for clarity.
Always Ask About Food Allergies
“I was helping a friend make food and get drinks ready once for a big date at his house. His date was a beautiful girl, green eyes and all. This idiot didn’t ask the girl if she was allergic to certain food groups (which, let me tell you, you should always do for life and death reasons). He then prepared a shrimp mince to stuff into chicken (sounds gross, but lots of people love it).
The girl came over, I said hello and wandered off upstairs to play PS4. Not FIVE minutes in, I heard shouting and panting. I ran downstairs and the girl was on the floor. My friend was next to her, losing his marbles, and she couldn’t breathe. I yelled at him to check the purse for an EpiPen. She had one and he administered. We called 911 and spend the next three minutes with this girl vomiting and cursing. What she once had in beauty all went into fine rage and a very pessimistic attitude.
The EMTs get there, we all explained what happened. She went off and my friend and I were left there looking at each other.
The chicken was delicious though. We ate the leftovers and called it a night.
To this day, he’s a sniper of a guy and always observes. I can’t speak for her though. I guess she was a bit of an airhead. Funny thing is, they talked again once, and she brought it up as though he was at fault. He said sorry, bid her well, and the conversation was dismissed.”
That’s Not His Mom
“There was this young guy eating dinner with who looked like his mom. I noticed they seemed weirdly uncomfortable and distant, but didn’t think much of it. Turns out the lady was not his mom. He had met her on a dating site and had been VERY clearly catfished. The lady was at least a good 20 years older than him.
When she left the restaurant, he stayed behind and told me about what happened then asked me out. I politely declined, but agreed with him that that was a really weird situation.”
“A few years back, I was working at Pizza Hut as a driver. We had the smallest store in the area, and there were no booths or tables for customers. You come in to pay and leave. There is one small bench barely able to seat two inside the door. This ‘couple,’ probably freshman, come in and the lad nervously orders a single medium pizza. The whole time ordering it, he was trying to be very literate and use a bunch of old English sounding phrases to sound appealing or smart or something. It started with stuff like, ‘Only the finest of topping for us,’ and devolved from there.
He spent the 10 minutes of cooking time crammed on that tiny bench with the girl, who was visibly uncomfortable, but also either too polite or too nervous to leave. I was hoping they’d leave and take it to a car or to the park, but no. He started trying to hand-feed her pizza on a bench too small to comfortably seat two with a few customers in line less than two feet in front of them, and drivers constantly having to step over their legs to get out of the store.
In-between the embarrassing ‘want another bite?’ she was practically shaking at this point and closing her eyes out of embarrassment. That was a big mistake, because he slipped in for a kiss instead of pizza. Regrettably, it worked, and she revolted and threw up on the rest of the pizza in his lap.
She bolted and ran off. He tried to order another pizza to go because ‘she didn’t get to finish it, she’ll like it if I bring her another.'”
They JUST Broke Up
“I used to tend bar and this one cute girl came in from time to time on dates. I always wanted to talk to her, but it’s tough to flirt with someone you only see when they’re with someone else.
Anyway, this one time she was sitting at my bar with some guy. I really wanted to talk to her, so I figured I’d just talk to them both, so she’d at least know I existed. I approached them and offered another round of drinks. They said, ‘No thanks.’
Then I said, ‘You guys make a cute couple.’
Without a word, she stood up and ran to the bathroom. Her date and I watched her go, then he turned to me and said, ‘Dude, I JUST broke up with her.’
She came out of the bathroom, had clearly been crying, looked at us both and walked out of the restaurant. She never came in again.
I ended up buying the guy another drink. He was cool.”
It Takes A Snob To Know One
“I witnessed this at a coffee shop in Melbourne. The man, about 25-ish was sitting two tables over when a woman around 30 walks over. He tells her ‘Sorry, I’m waiting for a date.’
She says ‘Yes, Jack, I am your date.’
Super awkward from the start. This guy then spends the first 10 minutes talking about the history of the coffee shop in such a condescending way before he even thinks to ask her a question. He then asks where she works. She starts to tell him about how she works in administration at the university when he cuts her off mid-sentence to talk about the degree he got there.
Another 15 minutes goes by, I’m on my second iced mocha because there’s no way I’m leaving now. He’s still describing his degree and neither of them have ordered (you have to go and order yourself at the register) when she tries to interrupt to ask about what he would like. He seamlessly switches into types of coffee he knows is the best and that you have to be an idiot to even consider ordering a latte when a cappuccino is obviously superior.
She just stands up, walks to the register while he angrily demands to know where she’s going, she orders a latte whilst staring at him. He looks so offended that this woman wouldn’t even take his expert advice and starts to tell her she’s made a mistake. She agrees and tells him that it was a mistake to meet with him, takes her latte, and tells him to never contact her again.
I finish my drink and overhear him on the phone telling someone that the woman was sooo self-absorbed and snobby. I almost couldn’t hold myself together before I left.”
He Messed Up Big Time
“My girlfriend and I sat next to an obvious first date at a Pan-Asian fusion restaurant (Zen in Durham, UK). She comments that her main course wasn’t quite what she expected and thought it’d be spicier.
He then snaps his fingers above his head VERY loudly so half the restaurant turns around to look. A waitress rolls her eyes and goes over. He demands that they COOK IT AGAIN AND MAKE IT HOTTER. Next thing, there’s half a dozen Thai waitresses around the table calling him worse than crap in Thai (my Thai girlfriend translated), causing a massive scene while her face turns red, and they take her plate away.
She then has to sit with no food while he continues eating. He eventually realizes he messed up and stops eating, but she sarcastically tells him to enjoy his food. They brought her a fresh plate, and they eat in silence.
I’m sure it was the first and last date.”
Would You Like Some Pasta With All That Cheese?
“I work at a nice restaurant. It’s not a 5 star Maitre D’ type place, but it’s not Applebees either. There’s a dress code. There’s mood lighting. And it certainly isn’t cheap.
I was waiting on this couple, who are clearly on a first date. The man seems initially delighted with her. I take their order and she orders the Fettuccine Alfredo. Cool no problem.
I bring their orders out and, as is custom at our restaurant, I ask the lady if she would like some fresh grated Parmesan on her pasta. She goes, ‘Oh yeah. I looooove cheese. Your arm is going to get tired I’m warning you!’ Her date smiles at her, clearly thinking she’s adorable.
Now, I’ve heard this and dealt with this before. I have grated a lot of cheese in my serving career. It’s never been a problem and I almost never judge someone’s cheese preference, being a dairy lover myself.
I will never forget this lady. I have never grated that much cheese before or since. It starts off normal and her date is still smiling at her. The pile begins to grow and he chuckles, clearly thinking this is some cute quirk.
But she doesn’t tell me to stop. You can no longer see any pasta on this dish and our dinner pasta portions are very large. I can see on his face that his initial delight with her is slowly morphing into surprise. The smile is growing smaller and tighter and the eyebrows are going higher.
And still she doesn’t tell me to stop. She’s clearly thrilled and obviously wants MORE cheese grated on this thing. For the first time, my arms and wrists start to hurt. Now there is nowhere left for the cheese to go but UP. A small humped mountain of Parmesan is growing on this woman’s plate. FINALLY, after what seems an eternity she says, ‘Okay! That looks great!’
I am not exaggerating when I say she was having some pasta with her cheese. I had to get a fresh block because it was worn to the nub. My wrists hurt like the dickens. A first for cheese grating in eight years. I don’t know how to describe it, but it came across as very…tacky. Like, our pasta is very good, it doesn’t need that much cheese. If I’d been on that kind of date and someone ordered their pasta dish like that it would be embarrassing and a turn off for me. Wanna eat wings or ribs and get sauce all over our bodies? To a sports bar it is! Oh…you’re gonna do that at a nice sit down? Um…
This dish looks absolutely gross. I look over at the guy’s face and it has now morphed again from surprise to pure disgust and embarrassment.
She is completely oblivious and digs into her cheese stack still chirping and chattering at him. He won’t even make eye contact anymore. The smile is gone. He is clearly over it. It’s very obvious there is not going to be a second date.
I skip asking if they want dessert and bring him the bill as quickly as I can without appearing to rush them. He gives me a look that all but screams ‘Thank You!’ and makes his excuses to go, leaving me a VERY nice tip for expediting this painful experience as much as was professionally possible.
I haven’t seen either of them back since.”
“I work at a cafe where we make cakes, sundaes, and other treats. It was a Friday evening shortly before Valentine’s Day. We got the usual busy crowd of couples and dates coming in for some desserts after dinner.
I was bringing some food to the tables when I noticed a couple come in. A woman dressed in a black dress, her hair done up all nice and fancy make up, looking absolutely ticked. She was followed by a guy, dressed casually, on his phone and wasn’t paying attention to where he was going. He was stopping every few minutes to text.
The girl placed her order, and every time she ordered something, she looked angrily at the guy, who just looked at his phone. The cashier and I shared a confused look at each other.
She must have ordered about 10 things and then went to go to her seat. I prepare the slices of cakes and bowls of ice cream, and look over at their table everyone once in a while. The guy was slouching in his chair, still on his phone and the girl was looking across the table at him with the glare of death.
I brought them their cakes. As I set down the tray, the guy finally looked up from his phone. He opened his mouth to say something, then just went back to staring at his phone. I walked away, but when I got back to the counter, the cashier put a hand on my shoulder and pointed over to the couple. I looked back to see the woman gobbling down all of the cake. She was ignoring the provided silverware and I didn’t even think she took a moment to breathe. I had never seen anyone devour so many pieces of cake like it before in my life. The guy was watching with as much shock as us.
My guess is the woman snapped and just didn’t care anymore. She walked to the counter with chocolate and cheese cake smeared on her face, looked at the cashier with crazy eyes before slapping a $50 bill onto the counter. She left in a hurry, and the guy sat there for what felt forever, with his phone down.
The weirdest shift yet.”
At Least Someone Had A Good Night
“I will look like a piece of crap, but whatever. This was about 15 years ago.
I was at a trendy restaurant late at night with a friend and beside us was a couple that was on their first date. The girl was hot and had a very sultry voice, which captivated me, I kept staring, that voice…
At some point, you could tell she was not interested. Twice she took calls and left the table. You could also tell the guy had figured it out, so he asks for the bill. The girl was still on the phone (later I found out with a friend begging for a ride), and the dude pays for the bill and vanishes.
On our way out, the girl was still waiting for a friend. I started chit chatting and did we connect. We mostly connected at how embarrassing that date was. We laughed for like an hour, she almost peed herself. I mean, my friend and I were half a foot away – it was like we were the 3rd and 4th wheel and that date was awkward as all get out.
She eventually tagged along with us. We met up friends at a nearby night club, and we ended up dating for like three years.”
Looks Like They Each Had Different Interpretations
“I love to go to this small noodle shop that’s always crowded. To save time and space, the waiters often put all different customers at the same table, therefore one table might have four different groups of people there. What’s more, is that the tables aren’t very spacious and there’s not much foot room. You are very close to everyone around you and can hear pretty much everyone’s conversation.
So, I came in one day during lunch rush with my grandma who only speaks Mandarin. The people sitting next to us were on what I assumed to be a date. They spoke much louder than my grandma and I, and didn’t seem to think I could understand them.
Anyway, the guy seemed a little nervous. The girl, not so much. They both seemed to get along fine. I listened to the dude talk throughout my meal and prayed that the date ended well for him. Judging his every move because from what I understood, the guy invited the girl, and he seemed to have planned everything.
I took a big bite of noodles and heard, ‘So what do you think of our date so far?’
The girl said, ‘Wait… we are on a date?’
I almost spat out my noodles hearing those words. For the next five minutes, the girl tried to explain that she’s not interested in a relationship and that she thought they were only eating lunch, as friends.
Rest in peace, brother.”
Pro Tip: Olive Garden Is Not A Fancy Restaurant
“Several years ago, when I was still in college, my roommate, friend, and I went to Olive Garden. Now I’m already not a huge Olive Garden fan, and this wasn’t a particularly amazing one to begin with, but the night started weird and got weirder as it went on.
First off, the entire restaurant is dead quiet and it is a Friday night. It’s weird that it’s empty considering we’re literally right next to a movie theater and mall. That should have the place bumping. The waiter sits us down in a booth and naturally the bread sticks start coming.
Not even before we get the menus, the guy sits a couple in the booth directly behind us. I suppose it’s to keep the two tables in the same area since there’s literally our table and them and our waiter doesn’t want to be running back and forth all night, but it’s still kinda odd he didn’t at least sit us one booth apart. The booths are super tall so you can’t really see over them unless you’re trying to or just really tall, but the funny part is that we’re sitting next to a glassed in booth area that’s reflecting our booth and the couple’s booth, so we can see them without actually having to crane our necks to look over.
Naturally, we can hear the entire date because it’s just two tables, and in the reflection we can see that the woman has dressed up for a much nicer restaurant than Olive Garden. The three of us are super casual because it’s a college town, and we’re next to a mall, but this lady is in a dress with heels. We can immediately tell she’s not happy, and she starts in on him. I don’t remember her exact words, but it went something like this:
‘I thought you said we were going some place fancy?’
We can hear the guy shifting uncomfortably in his booth because he’s sitting back-to-back with me and my roommate and the booths are made of loud pleather.
‘I mean, Olive Garden isn’t cheap,’ he replied nervously.
I look over at the reflection and he’s literally sweating like Charlie Day in that episode of ‘It’s Always Sunny’ where he’s also on a bad date. This guy is wearing a button up one size too big and he’s basically sweating so bad it’s like he’s running a marathon, but it’s dead of winter in Washington state, so it can’t be over 40 degrees out.
The couple starts talking in a low tone and the three of us order and get more bread sticks and start talking among ourselves. We almost forget about the couple behind us when my roommate elbows me and nods over to the booth again. We hear the lady going into a tirade about a guy named mark. Again, I can’t remember exact words, but it went something like this:
‘I mean, I keep trying to make plans with Mark, but he’s really busy at work and doesn’t text back in time, so it’s hard to plan with him. He’s really on my level and I think we’re really good together. He has a really good job he’s passionate about and he’s also really funny in a weird way. Do you know if he’s free next week?’
My table has to stop ourselves from dying because this lady is literally asking her date if their mutual friend is free. And this part I do remember well because I almost spat my drink out hearing it. The guy goes:
‘Are you really asking me if Mark is free on our first date?’
He sounds so sad and I felt so bad for him. And the girl has zero cares to give as she goes:
‘You told me we were going out to a nice restaurant tonight, but you brought me to Olive Garden and told me we were going to play Smash Bros at your brother’s after instead.’
I don’t know what happened after because they ate in silence for the rest of the date. We paid our bill before they did, but WHEW that was rough. As we walked by, the woman gave me a look that was halfway between ‘help me’ and ‘can you believe this guy’ and I nodded in response.”
It Couldn’t Have Ended Well
“I was on a work trip and was having dinner and a drink at the bar of a restaurant watching Monday Night Football.
About half-way through my dinner, a guy walks up beside me and orders a drink. He downs it real fast and orders another and again downs it real fast. The bartender asks if he wants another, and he says he’ll wait until his friend arrives.
Five minutes later or so, a lady shows up and they chat with pleasantries. I’m not really paying attention, but from what I see and hear, I can tell it’s a first date. I then overhear her ask if it was weird that she looked through his Facebook before the date. She was wondering if by his pictures if he’s really into weaponry.
At this point, I’m interested and start listening while focusing my eyes on the football game and also begin to text my wife a play by play. And so as they are talking, they get on to his past. I can’t hear everything, but I hear him say he hasn’t been on a date in 8 years and then I hear him speak about his old girlfriend who he says ‘wasn’t perfect, but was perfect for him,’ which I find weird to say to your date. Whatever, I’m married and maybe the rules of dating have changed.
He goes into this long story about how she was with someone before they met, but they fell in love anyway. Then he gets really choked up and I’m super uncomfortable, but also curious. He then talks about how she was murdered. He says the word ‘murdered’ four times, the last one with some emphasis. They start talking lower and I can’t hear as much, but it had something to do with her family in Ohio and a criminal family member.
At this point, I’ve been done with dinner for 15-20 minutes and I can’t imagine being more uncomfortable, so I leave. Maybe it works out for him with her, but I just can’t imagine bringing up your murdered girlfriend within 20 minutes of your first date in 8 years ending great.”