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

ICE agents at Atlanta airport
Megan Varner/Getty Images

The White House Just Tried To Rebrand ICE Agents As 'NICE Agents' With Hilariously Propagandistic Graphic

The White House was criticized for sharing an image to rebrand ICE agents as "NICE" agents, including a poster of an agent kneeling next to a child that has been condemned as blatant propaganda.

The decision came after President Donald Trump shared a post from a supporter urging him to change the name of Immigration and Customs Enforcement to National Immigration and Customs Enforcement, which would change the acronym from ICE to NICE. Trump said in a post on Truth Social it would be a "GREAT IDEA!!!"

Keep ReadingShow less
Screenshot of Jimmy Failla
Fox News

Fox News Reporters Caught On Hot Mic Joking About How Lax Security Was Before Correspondents' Dinner

Fox News reporters were criticized after they were caught on a hot mic joking about the unusually lax security at the White House Correspondents Association dinner before a shooting disrupted the event.

Their commentary followed a security scare at the Washington Hilton, where President Donald Trump and senior officials were quickly moved to safety after shots rang out outside the ballroom. Investigators believe the suspect fired one or two rounds. The Secret Service returned fire but missed, and the suspect was later apprehended near a staircase leading into the ballroom.

Keep ReadingShow less
Screenshot of King Charles shaking hands with Donald Trump
@AdamJSchwarz/X

Trump Just Totally Met His Match When He Tried His Macho Handshake On King Charles In Viral Clip

President Donald Trump was widely criticized for attempting his awkward tug-of-war-style handshake while greeting King Charles III at the White House on Monday, only for Charles to shut him down.

Charles addressed a joint meeting of Congress on Tuesday, becoming only the second British monarch to do so after his mother, Queen Elizabeth II, who spoke in 1991. His speech came as Trump has repeatedly criticized British Prime Minister Keir Starmer over Britain’s refusal to back the U.S.-Israeli war on Iran.

Keep ReadingShow less
Donald Trump
Alex Wong/Getty Images

Pastor Calls Out Christians Who Claim 'God Protected' Trump At Correspondents' Dinner In Spot-On Tweet

Reverend Benjamin Cremer, a pastor and writer who often comments on the intersection of politics and Christianity, called out MAGA supporters' reaction to the shooting on Saturday at the White House Correspondents' Association dinner and lamented the idolization of President Donald Trump.

Cremer's words followed a security scare at the Washington Hilton, where Trump and senior officials were quickly moved to safety after shots rang out outside the ballroom. Investigators believe the suspect fired one or two rounds. The Secret Service returned fire but missed, and the suspect was later apprehended near a staircase leading into the ballroom.

Keep ReadingShow less
Mara Wilson
Amy Sussman/Getty Images

Former Child Actor Mara Wilson Reveals Heartbreakingly Disturbing Reason That Led To Her Not Wanting To Act Anymore

You probably know her as Matilda or possibly as the youngest daughter, Natalie Hillard, in Mrs. Doubtfire, or maybe the inquisitive and too-smart-for-her-age Susan Walker in Miracle on 34th Street.

But for former child actor Mara Wilson, that's where most people's knowledge of her stops, and the reasons behind that are heartbreaking.

Keep ReadingShow less