11 Truly Awkward Blind Date Moments That Will Really Get You Cringing

Flickr / Daria Nepriakhina
Flickr / Daria Nepriakhina

Found on r/AskReddit.

1. I had just come back home from college and was having a night drinking at the local watering hole when I noticed the place had a new bartender. New attractive bartender. Short hair, nice tattoos that were clearly leading to interesting places and an Electric Six shirt. Fuck. Yes.

So I start making a bit of conversation, and much to my surprise, we seem to really hit it off. And not just bartender-is-everyones-best friend-until-they-leave hitting it off, but really cool conversation.

She starts hinting at if I’m seeing anyone, and I say no, and she immediately reaches into her pocket and starts writing something down.

“On top is the number at the apartment, and these are directions. We’re having a party on Wednesday night, and you should come.”

True enough, a phone number and directions.

What would you think?

Wednesday comes and I’m dressed up and ready to impress. I head over to her place, knock on the door and there she is, looking amazing. She smiles and hugs me, grabs me by the hand and drags me through the party until she gets to this big dude.

“Jonas, this is my roommate Jeff. Jeff, this is Jonas.”

I do the whole pleasantry thing, but when I turn around, she’s gone. I mean, poof. Gone. Like Batman.

Not knowing anyone else, I just keep on talking to Jeff. Seems like a good guy.

Suddenly he stops me mid sentence and says,”You’re not gay, are you?”


“You should really tell Liz that.”

She had apparently set up the entire part as an excuse to hook me up with her roommate. I had been on a blind date with a dude and didn’t even know.


2. I once went on a date with a girl and this is how the conversation went.

Her: “So whats your favorite book?” Me: “Tough, but when I was little I LOVED Jurassic Park” Her: “Yuck, Jurassic Park” Me: “The book or the movie? EVERYBODY loves Jurassic PARK!” Her: “I don’t believe in dinosaurs” Me: “Fossils?!??!??!” Her: “I don’t want to get into it but I think fossils are bullshit”

I ended the conversation there and held onto the night. Until later on she told me, “I don’t believe in outer space” and my head fucking exploded.


3. I wasn’t feeling great, but decided to meet anyway. We met at a Belgian beer bar. She was gorgeous, fun, and totally into me. I felt a gas pain, so I leaned forward slightly to quietly relieve the pressure. I completely and explosively shat myself. The odor was immediate. I excused myself to the bathroom, but the damage was too great. I walked out of the bathroom, muddy-panted, out of the bar, and boarded the train for home.

The date was nothing, compared to the horror of the following three weeks, recovering from E-coli.


4. I’ve only been on one blind date a few years ago. It was with the investment banker son of one of my mother’s friends. One of her attempts at finding me a respectable boy from a good family. So that night he calls to ask if I could pick him up instead since is car broke down. I thought, no problem, and asked where he lived. The guy was staying at a buddies place an hour from my house, ugh, but still no problem I thought.

So I get dress in my cutest little black dress and heels to channel the grace of Audrey Hepburn and, gosh darn it, I think I did well. I pick the guy up and he’s not all bad. A little on the short side but he has a cute face and seems fit.

So we get to the restaurant and order. He gets a few drinks into him and we have a conversation about jobs/stuff, but then it arrived at who we admired. His answer? Patrick Bateman from American Psycho, just, ya know, without the killing and stuff. He said he admired the character and aspired to live that kind of life (without the killing of course). DING DING DING…the alarm bells were going off in my head. So trying to change the subject I mention the frat that he was in (we both went to the same university) and that I knew some of the guys. He then proceeds to tell me that, yea all his friends were just vehicles for him to get ahead in life and that he didn’t really like any of them. Ooooook.

Then comes the check. He forgot his wallet. So I paid. Just awesome. By now I was just looking for this night to be done with, but no things had to get more fun. On the way back to the garage we pass by an alley and he leans in and whispers into my ear and says, “You’re fucking hot and I want to fuck you behind that pile of garbage,” and he LICKS MY EAR!

Waaaaaah blashhldflka Do Not Want! I tell him the night is over, gave him some money, and said that he could take the public transportation home. I then called my friends and went out to a bar to drink the experience away. Needless to say I was jumpy for a few days expecting an axe to come out from a corner at any moment.


5. I should really be working but I cannot resist typing up this story.

3-4 months ago I was talking to a girl on okcupid. Things were going pretty well and we decided to to get together. I was on a budget because I was saving to move out of the country, so I suggested as local thai place which had $0.25 cent beers with an entrée, figuring the food was pretty decent and the cheap beer wouldn’t hurt.

I offered to pick her up but she declined, which is completely respectable. The night of the date I’m running about 5 minutes late and feeling a bit rushed when I get a call from her. Even though I gave her an exact address in an easy to find place in town, she’s having trouble getting there. She ends up calling me back 6-7 times in the next 45 minutes as she tries to find her way there, no advice I could give was helping this girl. By this point I’ve already been there 30+ minutes and am about 3/4ths of the way through my first beer. Red flags about how incompetent this girl must be are going crazy, but I’m already on the ride. The final time she calls me she says “hey is there parking lot?” to which I reply “no, it’s all street parking, but there were a lot of open spots when I parked” she then replies “I don’t know how to parallel park”. Mind you this is a city, parallel parking is a way of life. I’m pretty dumbfounded that she doesn’t possess this skill.

This is already a nightmare in my mind, and as I sit there pondering how to solve it she asks if I would mind coming out to park her car. I agree and start walking outside, being a bit embarrassed at having to explain that I’ll be right back to the hostess.

I walk outside and a few minutes later she pulls up. First of all, this girl was not as advertised. I got myspace angled hard. I’m not someone who needs the perfect girl, but I’m telling you this was out of control. I climb into the drivers seat and the first thing I say his how weird it is. I tell her I haven’t driven anything but a manual in 3 years and her automatic feels very strange.

I slowly accelerate and head down the block, about 3/4ths of the way down I see an open spot. I let off the gas and instinctively go to push in the clutch. Instead, I stomped the brake. Hard. This girl had quite a lot of mass, and wasn’t wearing a seatbelt. Any physics student knows what happened next. Her head flies forward and nails the dashboard. I start apologizing like crazy, and luckily she wasn’t hurt. We spent the next hour having a really awkward dinner and then parted ways. No, we didn’t call each other.

– Anonymous

6. An OKCupid chick:
We talked for a few times. The photos were small and blurry but I got the basic idea- at least enough to set up a date since she lived about 10 blocks away. She was about 24 at the time and I was 28.

We meet at a bar and while she isn’t fat, she is more plump than her profile lead on but all in all, not anywhere near as bad as some of the girls discussed here. I knew nothing was going to come of it but had nothing else to do that night so I figured I could have some drinks and hit the sack before midnight.

Almost as soon as we met, she suggests we start taking shots of whiskey. This girl could drink! Over the course of a couple of hours she probably had a half dozen shots of whiskey and several mixed drinks. During the process she liked to discuss how much she loved giving blowjobs and how slutty she was. I guess she had self esteem issues, I dunno.

I was plastered – like blind drunk – by the time we are ready to leave. I don’t remember going to my apartment but I remember we ended up on my couch with a movie on as I faded in and out of consciousness and she raided my liquor cabinet.

What happens next would have landed me in jail if the roles were reversed:

First, I wake up to her on my lap. She is sitting facing away from me, grinding her (still in dress & panties) crotch against my jeans and stumbling about during the process…then things go black again….

I wake up again and this time it is to a blowjob. I might have been drunk but I remember a good blowjob and this chick was giving a great deep-throat, gagging blowjob like only a drunk girl and/or pornstar can…then things go black again…

I wake up again and now she has my pants around my knees, she had removed her panties and squatting over me fucking me with no condom. I remember being totally freaked out by that, but not as freaked out as when she removed her bra and a dusting of dead skin fell out of the cups and onto my black shirt. I literally threw her off of me as I stood up and ran to the bathroom with my pants around my ankles, puking my guts out into the toilet.

When I got back from the bathroom I was slightly sobered up and she was sitting on the couch masturbating. She asked if we could finish fucking and I said no but she could finish me with a blowjob if she wanted to. I honestly don’t remember if I came or not because I passed out again.

When I woke up the next morning she was gone and I never replied to another one of her text or OKCupid messages again.


7. I got set up with the daughter of one of my parents’ friends. I wasn’t really looking forward to it, but I was on break from college, and she apparently went to school not far from me, so it wasn’t like a lost-cause summer romance type thing. They showed me pictures and said nice things about her.

I picked her up from her parent’s place (we were both home for the summer) and was a little surprised by how pretty she was; the pictures had been from when she was in high school, and didn’t do her justice. The date was dinner and a movie. Dinner went really well; we had a lot in common, she was very grounded and down-to-earth, cared about the environment. If I have a type, she was it.

So as we’re walking to the movie theater, I slipped my arm around her waist. She pushed me away and got all serious. “I’m really sorry, because you seem like a nice guy, but … I’m a lesbian. I just went out with you to make my parents happy.”

Sitting through The Chronicles of Narnia with her was the most awkward two hours of my life.

– Anonymous

8. I was set up with a friend of my roommate’s girlfriend. Let’s call the date “Lisa” and lets call the roomy’s girlfriend “Karen”. I knew what she looked like so I knew there was an attraction but I had never spoken with her.

We met outside of the restaurant and Lisa was on her cell phone. I figured it must of been important but as we walked in and waited for the table she kept talking about stupid crap- clearly on the phone with a BFF about nonsense. She gets off the phone, doesn’t apologize and we get seated.

About 2 minutes later her phone rings again and it is the same “OMG, No Way!” crap conversations. The waitress comes over and we order drinks…while she is still on the phone and I twiddle my thumbs. The drinks come, Lisa is still on the phone…. I’m 1/2 done my drink and have waved the waitress off once already because Lisa is still on the phone.

Finally about 20 minutes into it I quietly stand up, take $20 out of my wallet and walk out without saying a word. As I’m walking out I see Lisa’s eyes widen to the size of dinner plates, her mouth open wide and her face turning red in embarrassment (all of the surrounding tables had seen what transpired and were whispering to themselves about it.)

By the time I got home, my date Lisa was on the phone with Karen who was over at our house at the time. It didn’t occur to me until now that my date was probably on the phone with Karen the whole time!

Karen was pissed. As soon as I walked through the door she started attacking me with “You are such an asshole, why would you just leave her there and not say anything!?!?”

I looked her dead in the eyes and calmly replied “I didn’t want to interrupt such an important phone call” and then walked into my room and went to bed. As I was leaving the living room I noticed the same expression on her face that Lisa had when I left the restaurant.


9. I went on a blind date two years ago with a guy one of my good friends set me up with. He just started university at USC and was majoring in Political Science. I thought he sounded pretty smart from what my friend told me and agreed. We met at Laguna Beach and had dinner at The Greeter’s Restaurant, which is this cute little place that doesn’t have the best decor, but has good food with large portions.

It was fine at first because he was cute and we had some things in common like music and traveling. It wasn’t until he started mentioning that he was a die-hard Republican and did not support gay marriage and abortions and IVF babies. I’m an IVF baby, and it’s a sore subject because my mom tried so hard to have a baby with my dad and it wasn’t until she tried IVF that she had me.

Stupidly, I asked him what did he have against IVF babies. He immediately spews on and on that IVF babies are nothing more than objects of status to their parents, that it violates the rights of the child, depriving him of his true relationship with his parents and can hinder the maturing of his personality etc.

By this point, I was done with the date and just nodded along to whatever he said. After he paid the check, he drove me home and walked me to the front door. I unlocked it and then turned around to say good night when he leaned in with his tongue already out. I didn’t know what to do so I tilted my head so he would hit my cheek. Worst feeling ever of tongue licking your face. When I went inside, he looked at me shocked, and asked if I was going to invite him in. When I told him no, he got pissed and said that “I paid for your fucking dinner!” By then, I just wanted to drink a bottle of wine by myself, so I took $10 out of my wallet, threw it in his face and closed the door.

Worst blind date ever.

– Anonymous

10. I was set up by a friend when I was 16. He took me to the movies (at the mall) and awkwardly tried to make out. Then we sat in the food court and he asked my honest opinion of him, which I mumbled something typical like “you seem nice.” Without invitation he then delved into what he thought of me, which was attractive but could be really hot if I lost 5-10lbs. Then he left me for a bit, which was weird, and returned with a lovely gift…a creepy puppet.

– Anonymous

11. I’ve only been on one real blind date. I met someone online we began chatting every few days, just kind of getting to know each other, or so I thought. She said she had just moved to the area, was staying with an old family friend but didn’t really know many people, so I suggested we go out to this little hookah bar that was about halfway between our respective places.

Eight p.m. rolls around and I pull up in front of her place, a townhouse in a nice neighborhood that happened to be a few blocks from where an old friend used to live. She was already waiting outside, which struck me as odd, but I figured maybe she felt like a smoke before leaving. She looked exactly like she did in her pictures – about 5’8″, maybe 120 lbs, long (dyed) blond hair, a few facial piercings. Not exactly my type, but not bad to look at either.

I get out, introduce myself and open the door for her and we’re off. Turns out we have similar taste in music, so the ride over to the bar was pleasant enough. I hadn’t been there in years, and was unaware they had hired a DJ to spin on Friday nights. You could barely hear a thing inside, so we chose to sit out on the tiny patio. We order drinks, she choose a shisha flavor and we continue chatting.

This, my friends, is where things begin to go downhill. She asked about my profession (reporter), so naturally I asked about hers, to which she replied “I’ve had the same job for about 3 years. Taking care of my kids.”

Children. This was an interesting development in that she had never mentioned being a mother in our previous conversations, nor did her figure seem to indicate that she was a mother of two, spaced just 2 years apart. Now don’t get me wrong, I don’t mind kids, but at the same time I’m not looking to get involved in a relationship with someone who already has children. Just a little young for that.

Having broached that particular subject, she begins to tell me, at length, about the father. Abusive, never around, with drug problem she apparently shared. I’ve smoked weed before, and tried my fair share of psychedelics, but these were hard drugs she was talking about. Things continue to spiral south, and I quickly realize that this particular individual is likely suffering from some serious mental/relationship issues. We finish our drinks and head back to my car, when she drops the line that sends me running for the hills.

“I’m not gonna sleep with you tonight, but I’ll probably get drunk and fuck you sometime soon.”

I’m now officially ready to put an end to this travesty of a date, but having never had any experience with blind dates was not entirely sure how to go about wrapping things up. It’s still fairly early, maybe 10 p.m. or so, and she is making it clear she would like to continue the evening. I’m racking my brain trying to figure something out, when it hits me: The Twins.

The Twins were an interesting pair, either the cheeriest individuals you could ever hope to meet or at each others’ throats, depending on when you happened to run into them. They liked to party and had a small house across town that I tended to frequent. I hadn’t been to their place in a bit, so I gave them a ring and asked if I could bring someone over. Thankfully they were in an amicable mood and invited us both over.

Now I’d mentioned I hadn’t been to The Twins place in some time, so the fact that they had acquired a new roommate who was sleeping in the unfinished basement. We arrive, and one of The Twins suggests giving her the grand tour. Eventually we make our way to the basement, when lo and behold, another one of her apparently numerous ex’s is stretched out across a bare mattress on the floor.

This is the moment I knew I was saved: Before the guy even has a chance to get up, she dashes across the room, throws herself on the bed and starts hugging him, saying how much she missed him. My friend gives me a look of concern, being currently unaware that the chick is batshit crazy. I grin and whispered under my breath, “good, she’s his problem now.” Thought Catalog Logo Mark


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Brian Gates

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