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35 People Are Sharing Their Most Awkward Dates And It’s Both Funny And Painful To Read
We all deserve love and to be loved. I mean, is it too much that we’re asking for? But if you've ever walked in the shoes of a singleton, and at some point we all have, you know what a blessing and a curse it may be. Let’s face it, the dating game is not for the faint-hearted, no matter what the media and apps that people download and delete in a cycle of despair and hope would tell us.
In fact, a Pew Research survey showed that most of those on the romantic hunt, which makes up 15% of American adults who are single and looking for a relationship, are dissatisfied with their dating lives. How come?
Well, the answer lies somewhere between the lines of real-life stories from people who survived the most awkward date. And although the degree of awkwardness varies substantially from one date to other, anyone who’s had a bad one came out of it with a fun (hopefully fun) memory to talk about.
Thanks to Twitter user Steven Glansberg, who asked “What’s the most awkward date y’all ever been on?” we now have a collection of honest answers that tick all the boxes for a well-made drama film. Psst! After you're done, make sure to check out our previous post with the worst first date stories right here.
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#4
Anna Banana 5 years ago
Not an ideal date situation but at least his parents are happy. It has to be better than learning that mom is cheating on dad.
#5
Dan Buczynski 5 years ago
You got the assignment wrong. This thread is for bad dates only. This one sounds awesome.
#7
Tara Brooks 5 years ago (edited)
I adore her! Now I’m curious who it was... I looked it up. His name is Mark Anthony "Gator" Rogowski
#8
I want cake 5 years ago
Wow, that's toxic as all hell. Using your children to guilt women into camping home with you, is just terrible. I feel really sorry for that kid.
#9
Dan Buczynski 5 years ago
How long do you think he sat there, timing your "bathroom break" before he realized what happened?
#11
Dan Buczynski 5 years ago
This could easily be one that ended in "and we were married a year later"
#20
CrunChewy McSandybutt 5 years ago
Sounds like the pastor was c**k blocking you for his own selfish reasons.
#21
#31
Everything AGR 5 years ago
not sure if i should upvote cuz it fits the title or downvote cuz bruh
#32
WilvanderHeijden 5 years ago
In his mind you already proved that you're very rich, so you surely wouldn't mind buying him a ps5. Logic....
#33
Candace Fitzpatrick 5 years ago
As much as I agree that this person dodged a bullet, I find it really weird when people go to a restaurant and don’t order anything.
#38
Arctic Fox Lover 5 years ago
Yeah, the whole "Kids calling me stepmom" jazz might work in a cheesy movie, but DO NOT let your kids do this irl :0
#39
Hermien Greeff 5 years ago
So the most awkward date should be her story, not yours. Psychopath at works stalks me until I agree to go out with her son, hoping I can convince him to get her to stop.
#44
Anna Banana 5 years ago
Definitely out of line with that comment, but I appreciate the attempt at self-deprecating humour.
#45
Carol Emory 5 years ago
I would have turned to the women and said "If anyone wants a real meal, be at my car in 2 minutes." Leave the men to do the dishes and to figure out why they are alone. Plus, I'd like to know who cooked it. If it was the women...I'd just stop cooking for them.
#52
Dark_flame 5 years ago
I really don't get bragging about their criminal record, some ppl use that as a pick-up line!!
#55
Arctic Fox Lover 5 years ago
I wonder why it couldn't have lasted longer. Well, I know one thing for sure, her presence made everything so much better and didn't make things awkward and uncomfy whatsoever! 🤪
#65
M O'Connell 5 years ago
Flying roaches and fragile drywall are both pretty common in Florida. Nothing forgives a filthy house on a date though.
#72
Minha Khan 5 years ago
They may have been polyamorous (hopefully I spelled that right, I disabled autocorrect because darn you autocorrect), but she still probably should have written that in her bio if this was a dating app.
#79
Kimberly Young 5 years ago
The day after a first date, we were texting about setting up a second date. I jokingly mentioned that there was a strip club down the road from where we had dinner the night before. He said it wasn't his thing, but he'd go if I wanted to. He was pretty relieved when I said I was joking. We've been married almost 3 years.
#80
brukernavn340 5 years ago
I get it. Personally I prefer listening to music only when I can devote my full attention to it, so I don't listen to music that often.
#81
WilvanderHeijden 5 years ago
So the most awkward date should be his story, not yours. I took girl out to the movies, she slept until the movie was over and everyone was walking out.
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Linda Haney 5 years ago
I was asked on a first date to a party. I really liked this guy so to make his drive shorter I told him to pick me up at my mom' house. I got ready at my place, favorite jeans and a cute sweater. He picked me up dressed to the hilt. Turns out we were going to a ritzy wedding reception it an upscale neighborhood. This guy made a quick stop on the way to change into jeans. We were the only two dorks in jeans on fancy pants occasion. Pretty sure that's reason I married him. Now it's 38 years, 3 kids and 8 grandchildren later. Yeah, I got one of the good ones.
Legen ( wait for it ) dary 5 years ago
THIS WENT : what a silly take a date party, without telling its a weeding TO awww that's so sweet. Yes, you definitely got one of the good ones. Wish you happiness and health.
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jknbt jknbt 5 years ago
I joined a dating service with so many pretty ladies. One of them picked me, so I gave her a call. We had a basic "dinner & movies" type date. She was agitated and overreacted to everything I said during dinner. She said she was a nurse at a nearby psychiatric hospital for the criminally insane. She explained she was acting a little weird because she was cooped up with psych patients every day, and it rubs off. I was so nervous, I started to walk out twice. After the movie, I dropped her off at her apartment. No invitation to come in, no problem, I wanted to get out of there. So I called the psych hospital a couple of days later since she didn't give me her number. I wanted to thank her anyway for going out with me. I asked if I could speak to Nurse XXXX. The phone went quiet for a moment, and then the receptionist said, "Sir, we don't have a nurse by that name, but we do have a patient. Do you want to speak to her?" Apparently, she was out on a weekend pass. Yikes!
MrTir 5 years ago
Oh my. One the other hand it looks like she did all in her power to have one single normal date. I kind of feel sad about it.
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GirlFriday 5 years ago
I have so many of these. I think the one that fits this one is this: Met a guy online, we meet for coffee, hit it off and agree to dinner a few says later. We meet at a restaurant near a mall and have an hour to kill before our reservation so we go window shopping. He stops in a shoe store and wants to buy me a pair of shoes, I decline because I don't know him well enough to accept gifts and he becomes very insistent almost to the point of anger. Then he tells me that I wouldn't get to keep them anyway, he wants to buy them, have me wear for the date and then he will take the shoes home with him. Um...I noped right out of there and didn't even go have dinner with him.
Kate Fei 5 years ago (edited)
I met this guy online, he seemed sweet and attentive. Because he knew I liked cats he invited me for a date in a cat cafe. The first thing he said to me was that he hated coffee and ordered a bottle of beer. Then another one and another one. While I was slowly drinking my first lattee he had 4 beers and he was getting tipsy. Then he started to say how he hates woman, because his mom kicked him out of the house because he was doing drugs and then his girlfriend kicked him out of the house because he was cheating on her. He said because of those b*tches he must live with his friend. Then as he was getting drunk he ordered a cake and then started to throw pieces of the cake to the cats around him, calling them b*tches. Then he said his friend, who is also his drug dealer, is in the neighbourhood so he could join us. And indeed a few minutes later the friend showed up. After that I really wanted to leave so I headed out. He said it was an amazing date and we should do it again. We didnt.
AzKhaleesi 5 years ago
I have two. I'll make it short, one guy took me out for my birthday, didn't let me get a word in edgewise then took me "shopping" for my birthday.... at goodwill. Don't get me wrong, LOVE goodwill but come on. Second. Met a guy hung out at his place got late, fell asleep on his couch. Woke up with a friggin ring on my hand. I noped out.
Leo Domitrix 5 years ago
The worst ever.... Being on the third date before I realized I was, in fact, dating the guy. We'd been friends for 2 years, and I apparently missed the road sign that said, "This is now a date, not hanging out". Married almost 30 years, so obvs, it worked, but dang!
JCRocks 5 years ago
We were in a restaurant where there were TVs on the wall. He starts watching the news and making comments. The first story was about a nursing shortage. He starts ranting about how the "real problem" in this country are people like nurses and teachers who b*tch that they're being paid too little, when they should just shut up and be grateful they have jobs. "The reward of helping people should be enough. Teachers unions are ruining this country." I am an underpaid teacher. I knew it was done at that point, but thought I'd politely sit through the rest of dinner... And then there was a news story about a coach who was going to jail after having sex with a 16-year-old girl on his team. My date says, "He shouldn't have gotten in trouble for that. It's not like she's 12. These girls know what they're doing." Nope! I said, "This isn't going to work out" and left. In my car before I leave, message back this other guy who just asked me out. WE fell in love & have been married 4yrs
KT 5 years ago
My worst date, was about 20 years ago now i think. Had been talking to a guy online for about 6 months and we really seemed to click. I suggested we meet up for a date and see how it goes and he agrees. So he picks me up at my place for a movie. He'd sent me a picture online and let me say, not even close. He had a hunch back...not just a little one either. He was cross eyed and grossly over weight. I felt so duped. At the movies and the drive he didn't say one SINGLE word, nothing. I tried making conversation several times and he never engaged. After the movie he took me home and asked if he could come in. I said "no, this was a bad date, you didn't speak once i think you need to go". He was sitting in his car a little on my parents lawn/sidewalk for like half an hour. When he finally left he freaking peeled out on my parents grass. The next morning he sends me an online message saying he had such a great time and wanted to see me again LOL
Linda Haney 5 years ago
I was asked on a first date to a party. I really liked this guy so to make his drive shorter I told him to pick me up at my mom' house. I got ready at my place, favorite jeans and a cute sweater. He picked me up dressed to the hilt. Turns out we were going to a ritzy wedding reception it an upscale neighborhood. This guy made a quick stop on the way to change into jeans. We were the only two dorks in jeans on fancy pants occasion. Pretty sure that's reason I married him. Now it's 38 years, 3 kids and 8 grandchildren later. Yeah, I got one of the good ones.
Legen ( wait for it ) dary 5 years ago
THIS WENT : what a silly take a date party, without telling its a weeding TO awww that's so sweet. Yes, you definitely got one of the good ones. Wish you happiness and health.
Load More Replies... jknbt jknbt 5 years ago
I joined a dating service with so many pretty ladies. One of them picked me, so I gave her a call. We had a basic "dinner & movies" type date. She was agitated and overreacted to everything I said during dinner. She said she was a nurse at a nearby psychiatric hospital for the criminally insane. She explained she was acting a little weird because she was cooped up with psych patients every day, and it rubs off. I was so nervous, I started to walk out twice. After the movie, I dropped her off at her apartment. No invitation to come in, no problem, I wanted to get out of there. So I called the psych hospital a couple of days later since she didn't give me her number. I wanted to thank her anyway for going out with me. I asked if I could speak to Nurse XXXX. The phone went quiet for a moment, and then the receptionist said, "Sir, we don't have a nurse by that name, but we do have a patient. Do you want to speak to her?" Apparently, she was out on a weekend pass. Yikes!
MrTir 5 years ago
Oh my. One the other hand it looks like she did all in her power to have one single normal date. I kind of feel sad about it.
Load More Replies... GirlFriday 5 years ago
I have so many of these. I think the one that fits this one is this: Met a guy online, we meet for coffee, hit it off and agree to dinner a few says later. We meet at a restaurant near a mall and have an hour to kill before our reservation so we go window shopping. He stops in a shoe store and wants to buy me a pair of shoes, I decline because I don't know him well enough to accept gifts and he becomes very insistent almost to the point of anger. Then he tells me that I wouldn't get to keep them anyway, he wants to buy them, have me wear for the date and then he will take the shoes home with him. Um...I noped right out of there and didn't even go have dinner with him.
Kate Fei 5 years ago (edited)
I met this guy online, he seemed sweet and attentive. Because he knew I liked cats he invited me for a date in a cat cafe. The first thing he said to me was that he hated coffee and ordered a bottle of beer. Then another one and another one. While I was slowly drinking my first lattee he had 4 beers and he was getting tipsy. Then he started to say how he hates woman, because his mom kicked him out of the house because he was doing drugs and then his girlfriend kicked him out of the house because he was cheating on her. He said because of those b*tches he must live with his friend. Then as he was getting drunk he ordered a cake and then started to throw pieces of the cake to the cats around him, calling them b*tches. Then he said his friend, who is also his drug dealer, is in the neighbourhood so he could join us. And indeed a few minutes later the friend showed up. After that I really wanted to leave so I headed out. He said it was an amazing date and we should do it again. We didnt.
AzKhaleesi 5 years ago
I have two. I'll make it short, one guy took me out for my birthday, didn't let me get a word in edgewise then took me "shopping" for my birthday.... at goodwill. Don't get me wrong, LOVE goodwill but come on. Second. Met a guy hung out at his place got late, fell asleep on his couch. Woke up with a friggin ring on my hand. I noped out.
Leo Domitrix 5 years ago
The worst ever.... Being on the third date before I realized I was, in fact, dating the guy. We'd been friends for 2 years, and I apparently missed the road sign that said, "This is now a date, not hanging out". Married almost 30 years, so obvs, it worked, but dang!
JCRocks 5 years ago
We were in a restaurant where there were TVs on the wall. He starts watching the news and making comments. The first story was about a nursing shortage. He starts ranting about how the "real problem" in this country are people like nurses and teachers who b*tch that they're being paid too little, when they should just shut up and be grateful they have jobs. "The reward of helping people should be enough. Teachers unions are ruining this country." I am an underpaid teacher. I knew it was done at that point, but thought I'd politely sit through the rest of dinner... And then there was a news story about a coach who was going to jail after having sex with a 16-year-old girl on his team. My date says, "He shouldn't have gotten in trouble for that. It's not like she's 12. These girls know what they're doing." Nope! I said, "This isn't going to work out" and left. In my car before I leave, message back this other guy who just asked me out. WE fell in love & have been married 4yrs
KT 5 years ago
My worst date, was about 20 years ago now i think. Had been talking to a guy online for about 6 months and we really seemed to click. I suggested we meet up for a date and see how it goes and he agrees. So he picks me up at my place for a movie. He'd sent me a picture online and let me say, not even close. He had a hunch back...not just a little one either. He was cross eyed and grossly over weight. I felt so duped. At the movies and the drive he didn't say one SINGLE word, nothing. I tried making conversation several times and he never engaged. After the movie he took me home and asked if he could come in. I said "no, this was a bad date, you didn't speak once i think you need to go". He was sitting in his car a little on my parents lawn/sidewalk for like half an hour. When he finally left he freaking peeled out on my parents grass. The next morning he sends me an online message saying he had such a great time and wanted to see me again LOL
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