15 Incredibly Embarrassing Moments From Dates That Made People Die Inside

4 years ago

There comes a time in everyone’s life when you find yourself on a date so unbelievably awkward that you wish you could be put out of your misery as soon as possible. But keep in mind that while you may have to endure some uncomfortable silences or silly conversation starters, there are always people who survived worse moments that you could never even imagine.

So no matter how embarrassing your own experience was, it won’t seem so bad after reading these 15 date moments compiled by Bright Side.


We met up at a local burger joint and he didn’t say a single word. I asked questions and he responded with head nods and an occasional chuckle which was more like a release of air. I was pretty sure he hated me so, I told him I was just going to go home. That’s when he finally spoke. He asked me why and told me to please stay, so I did and he continued to sit in silence. Looking back now, I realize he was just nervous but man, at the time I really thought that I must’ve been horrible to be around. Update: We’ve been together for 2 years and he actually talks to me now.

— Foogliwoogli/reddit


I was walking ahead of him and got into the car parked out front before he could open the door for me. He knocked on the window and yelled through the glass, “This isn’t my car!”

— AnnaKrukCorbin/twitter


A few years ago I was dating a man about 25 years my senior. He invited me to go to a museum. He lived in Los Angeles and I lived outside the city, so the plan was to meet him in LA, then he would drive. When I got there he informed me that our next stop would be to pick up a female client of his from his financial planning business because she also had an interest in seeing this museum. So we picked her up and the 3 of us went on a date!

The funny thing is that she was really nice and we had a great time! My date paid for my meal and she paid for herself. My relationship with this man was sort of semi-romantic but never quite got off the ground in terms of heading toward marriage. I do have pleasant memories of that particular date though.

— Trubea/reddit


Met a guy on Tinder and we hit it off. The date was going GREAT. We had kissed a bit and were just really enjoying each other but I had to get home because I had work very, very early. So we’re putting our numbers into each other’s phones and I hand his back and he goes, “Is your dad Bob _________?”

I have a very unique last name.

I say yes.

My dad fired this guy a month ago.

— Venus_in_faux_furs/reddit


At dinner, my date asked what my ideal guy was, then whispered “yes” after everything I said.

— Megsmith06/twitter


Third date with a dentist and he’s a great guy! He’s handsome, volunteers with animals, and is funny. Went back to his place to watch a movie. He turned on his 52-inch TV and there was a picture of me from Instagram blown up and zoomed in on my teeth. He immediately apologized but I was horrified. He later explained that it was his favorite picture of me.

— Marniccal/reddit


In college, I got invited to a girl’s house for a “home-cooked” meal. The recipe called for 2 cloves of garlic and she used 2 HEADS of garlic. I sweated out garlic for a month! But all’s well that ends well — we’ve been married for almost 30 years and she still can’t cook!

— GerryCarlin/twitter


On our third date, he complained about his troubles with online dating and said that all the women in our city were too shallow and stuck up to date him.

I was not really feeling that line of conversation but I also understand that all that dating can do a number on one’s outlook. So I told him that I was sorry he’d had a rough go at online dating, but on a very selfish level, I was glad he wasn’t out on a date with any of those other women because I found him attractive, intelligent, and funny and I was excited for the chance to get to know each other better.

He smiled. Then he asked me why attractive women never go out with him.


— Caroline_Bintley/reddit


The first time I met my wife, she was convinced there were 52 states in the US. When I suggested there were only 50 states, she called her brother who confirmed that there were, in fact, 52 states.

— Hotovy/twitter


I went on a date to a pretty nice restaurant and when the check came, my card got declined. I tried another credit card that I hadn’t used in a very long time and that got declined too. Apparently, there was some fraudulent activity on my account. My date didn’t have her wallet on her so I had to run home, leaving her at the restaurant, while I got my roommate to spot me cash. We both agreed it’d be the easiest if I just stepped out and she stayed behind so they didn’t call the police or anything. But that must’ve been an awkward 45 minutes for that poor girl. I got things straightened out and we actually went on a few more dates but I felt awful leaving her behind.

— Kevin/Cosmopolitan


I met a guy online and we saw a movie on our first date. At the end of the night when he was acting like he was going in for a kiss, he put his whole mouth over my nose and blew into it. He started laughing and said he does this to his dogs and calls it a “puppy trumpet.”

— Snooki-cookie16/twitter


My friend Liz: Hey guys!

Me and Sarah (surprise): Oh! Hi Liz!

Liz: Are you on a date?

Me (instantly): Yes.

Sarah (instantly): No.

— Silence —

— Gabriel Gn Jianlun/Quora


The date was so bad I gave the server 20 bucks to spill my drink on me to get me out of there. #worstfirstdate

— Mummewummie/twitter


My date took me to a nice restaurant. Our server leaned in and said, “You’re the third one this week.”

— JessieB365/twitter


She brought a plastic baggy to puke in because she gets nervous on first dates...and she used it.

— DarinKingIsMe/twitter

Which one of these stories made you laugh the most? Do you know someone who’s had an even more embarrassing experience? What’s your own most awkward dating story?

Preview photo credit marniccal / Reddit


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Remind me of when me and my girlfriend first started dating, not like anything special happened, it just reminds me of a happy time ??


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