Skip to content
Search AI Powered

Latest Stories

People Reveal The Most Awkward Moment They Ever Had On A First Date

Reddit user Valana_Kayi asked: 'What's the most awkward or embarrassing moment you've ever experienced on a first date?'

Dating is one of those things where it can be totally worth it to put yourself out there or it can earn you a basket of rotten eggs.

There's really no in-between, and there's no telling what you're going to get until you're on the date.


But sometimes even when things are going fairly well and we're having a nice time, something embarrassing might sour the mood.

Cringing in anticipation, Redditor Valana_Kayi asked:

"What's the most awkward or embarrassing moment you've ever experienced on a first date?"


The Most Awkward Burger Around

"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 occasionally a chuckle that's 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 then 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 have been horrible to be around."

- SexyTara435

A Real Snooze Fest

"It was one of those setups where my mom and his mom were friends and they were like, 'Our two nerdy, intensely introverted loner kids should date!'"

"Unfortunately, that was the literal entirety of what we had in common, so."

"Bonus detail: we went to a theater that was showing 'The Big Sleep.' Quite fittingly, he fell asleep."

- Heavy-Research8837

Exposure Therapy On The First Date? Brutal.

"I took him for a picnic in the park- I used to go there all the time and was very comfortable with the geese, to where some let me pet them for snacks."

"I thought it would be cool of me to show off this skill and maybe get him the experience of petting one."

"I called over the geese for snacks without consulting him, and he ran for it."

"Turns out geese are his biggest fear, and seeing an entire flock of them running toward us at full speed was his worst nightmare."

- Velmabutgoth

Location Location Location

"This guy said he was taking me to the best restaurant in his hometown, which was like an hour away."

"He ended up taking me to his mother’s house where she had prepared a very nice dinner, but man, it was awkward as h**l. I did not accept a second date."

- Tonubba-nabubba

Sorry, Kathryn.

"I was at a house party, and the girl hosting pulled me into her parents' bedroom. We were kissing and fumbling around like teens do on her parents' bed."

"I took her pants off and for some reason, said something like, 'Do you think your dad does this to your mum here?'"

"The mood died pretty quickly after that. I still cringe when I think about it."

"If you're reading this, I'm sorry, Kathryn. It was and still is the most embarrassing moment of my life."

- BraveBeauty_

A Bonding Opportunity

"I farted in his car in the middle of summer with the AC off. Tomorrow will be five years together, so.."

- iOawe

"It was at that moment when your belly was empty that his heart was full."

- caughtinatramp

What A Neon-Glowing Nightmare

"My very first date in high school became embarrassing the moment my 'date' walked in. Neither of us drove, so we were dropped off at a bowling alley."

"My date walked in with her friend that she wanted to set me up with. I knew her friend very well, and I did not like her at all because she was not a nice person."

"So, I got to spend two hours with a super annoying mean person that liked me, while the sweet, kind, and cute girl that I thought we were going on a date made it clear in no uncertain terms that she was not interested."

- TroubledWaterBridge

That's One Way To End A Date

"While walking in the park, my companion offered to feed the ducks."

"Then one of the ducks attacked us."

- Lula_Niki

Two Strikes Is Fine

"This was embarrassing at the moment, but it worked out."

"It was a second date, but it was also Valentine's Day, so I decided to get her flowers, a card that played music, and some chocolates. It was freezing cold, but I didn't have anywhere to keep them besides my car. I took the chance the flowers might die."

"We had a nice date, and when we got back to my car, I got them out. Oh, those flowers were DEAD."

"'Ah well...' She opened the card, and the sound chip just went 'bbbzzzzzzzz.'"

"I sighed and said, 'Well... I hope the chocolates are okay.' She started laughing and gave me our first kiss."

- Worick4

You Don't Say...

"When she mentioned that she 'should have known her ex-boyfriend was gay' because he wore Express... while I was sitting across from her wearing an Express shirt and Express jeans."

- EchoedJolts

Not On The Same Level

"We talked on the phone quite a bit before the first meeting, like three or four times for a good hour or so at least. We also had pics of each other (only safe-for-work ones)."

"When we met, all mutual attraction somehow was gone, and we barely talked at all. Super awkward."

"It didn't even last an hour, we shook hands and were both 100% certain that this was the last interaction. Which it was. But that's a-okay."

"Not even a case of catfishing on either side. It just didn't work out on some higher level."

- Medium9

Totally Forgot

"I totally forgot my wallet by mistake on a first date one time. That was super embarrassing, and I felt really bad about it."

"She was nice about it and paid for the food, but I was worried she might think I was duping her. I wasn’t joking, though. We never had a second date, either. Lol (laughing out loud)."

"Another time, my ex wanted to rent a DVD from a Redbox. We drove to a CVS that had a RedBox, only for me to realize that I didn’t even have a DVD player at home anymore."

- I_like_cake_7

A Surprising Bought Of Grief

"It was me. We were having a great time, we had a couple of cocktails, and we were laughing constantly and flirting. I don't think I've ever hit it off so well with anyone."

"I'd not long come back from Afghanistan, and she asked about the temperature out there."

"Two minutes later, I was crying my eyes out, and all my s**t that I'd bottled up was coming out. She got all the details that she never asked for, and it was awkward to the point where she couldn't leave as I kept talking and crying, for one and a half hours."

"One hour of hilarious drinks. One and a half hours of crying and talking about dead children."

"So yeah, I didn't get a second date. I hope she's doing well. I really liked her."

- Banditofbingofame

Someone In Common

"It turned out we'd both been seeing the same girl prior to the two of us meeting. At the same time."

"We got to talking about specifics, and there were times one of us would see her in the morning or afternoon and the other at night."

"A few times, we figured, she'd gone right from my place to the other girl's."

"It was lowkey pretty funny, looking back on it."

- johnbmason47

A Loyalty Test

"He picked the coffee shop, a little boutique place. I showed up dressed to the NINES. Full pretty."

"I ordered the worst tea (dandelion) I've ever had. An hour passed. I contacted him."

"HE WAS AT AN ENTIRELY DIFFERENT COFFEE SHOP HALF AN HOUR AWAY. Not the same name, not the same brand identity, and nothing in common with the coffee shop HE CHOSE."

"He offered to come meet me. A staff member checked on me after I declined. I informed them the tea was much better than my date at this point, and called a friend to pick me up so we can do a post-mortem on what the f**k just happened."

"I did not finish my dandelion tea."

- WadeStockdale


Remember what we said about dating being worth it to put ourselves out there?

Yeah, after reading these, maybe it would be better to stay in this weekend.

More from Trending

People Explain Which Professions They Avoid Dating Altogether

When it comes to dating, most of us have an idea of the type of person we'd like to date, including certain physical attributes and interests.

But some of us go so far as to have workplace wish list items, including the professions we'd never consider dating.

Keep ReadingShow less
Donald Trump Jr. and MAGA supporters during his visit to Greenland
@DonaldJTrumpJr/X

Greenland Official Rips Don Jr.'s 'Staged' Visit, Says Trump Was Flipped Off By Locals

Pipaluk Lynge-Rasmussen, a member of Greenland's parliament, called out the "staged" nature of Donald Trump Jr.'s visit to the island territory, even reporting that he and his entourage were flipped off by locals at the airport.

Lynge, who stressed that Greenland wants “our own independence and democracy” and not be beholden to the U.S., spoke after President-elect Donald Trump’s eldest son flew to Greenland and met with locals he claimed are supportive of the U.S. taking it over.

Keep ReadingShow less
Pamela Anderson; The Chicks
Aeon/GC Images; SAUL LOEB/AFP via Getty Image

Pam Anderson 'Almost Got Killed On A Plane' After Man Mistook Her For Member Of The Chicks

Actor Pamela Anderson talked recently in a podcast about a harrowing encounter on an plane back in the 2000s.

Anderson, talking with the Happy Sad Confused podcast at the 92Y venue in NYC, concluded nearly an hour of conversation with a harrowing story of political obsession and mistaken identity that had her terrified in her seat of a plane.

Keep ReadingShow less
Firefighter extinguishing a home fire with @DogRightGirl's X that reads: 'The disconnect is jaw dropping. Just wow.'
Tayfun Coskun/Anadolu via Getty Images, @DogRightGirl

LA Real Estate Investor Sparks Debate With Offer To Pay 'Private Firefighters' To Save His Home

A Los Angeles businessman sparked backlash by writing a post on his now-deleted X (formerly Twitter) account offering to pay private firefighters "any amount" to save his mansion in the Pacific Palisades amid the raging LA wildfires.

On January 7, Keith Wasserman, a real estate executive and co-founder of Gelt Venture Partners, asked:

Keep ReadingShow less
Screenshots of LA parking officer issuing parking ticket
@Osint613/X

Video Of LA Police Officer Still Giving Out Parking Tickets Despite Wildfires Divides Social Media

Thousands of Los Angeles County residents have been forced to evacuate to avoid toxic air inhalation and the encroaching wildfires that have destroyed more than a thousand homes and businesses across the region.

So far, five people have lost their lives. Two of the largest active fires, the Pacific Palisades and the Eaton fires, remain designated 0% containment zones as firefighters continue efforts to extinguish raging flames.

Keep ReadingShow less