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

Screenshots of Justin Bieber being hounded by paparazzi
X17OnlineVideo

Fans Defend Justin Bieber After He Confronts Paparazzi For Constantly Hounding Him

Fans defended Justin Bieber after he berated the relentless paparazzi and accused them of only being concerned with turning a profit over valuing people's lives.

According to X17, the "Intentions" singer's retreat to Palm Springs, days before the Coachella Valley Music and Arts Festival, was anything but relaxing as he clashed with the paparazzi for a third day in a row.

Keep ReadingShow less
RFK Jr.
Kevin Dietsch/Getty Images

RFK Jr. Slammed After Claiming HHS Will Discover The Cause Of 'Autism Epidemic' By September

U.S. Secretary of Health and Human Services Robert F. Kennedy Jr. declared that scientists would determine the cause of the "autism epidemic" by September, even though scientists haven't discovered a breakthrough despite decades of research.

In a cabinet meeting with Republican President Donald Trump on Thursday, RFK Jr. stated:

Keep ReadingShow less
J.D. Vance and Usha Vance listen to Susan Meyers during his Greenland visit
Jim Watson/Pool/AFP via Getty Images

Space Force Commander Fired Over Email Criticizing Vance's Greenland Comments

Vice President J.D. Vance and the wider Trump administration are facing criticism now that Colonel Susan Meyers was removed from her post as commander at Greenland's Pituffik Space Base after breaking with Vance in an email she wrote following his controversial visit to the island territory.

Greenland is an autonomous territory of the Kingdom of Denmark, alongside the Faroe Islands, the only other autonomous territory within the Kingdom. Citizens of both Greenland and the Faroe Islands are full citizens of Denmark. As one of the Overseas Countries and Territories of the European Union, Greenland’s citizens are also recognized as EU citizens.

Keep ReadingShow less
Karoline Leavitt and Scott Bessent
Anna Moneymaker/Getty Images

Karoline Leavitt Dragged After Making Mind-Numbing Claim About Trump's Tariffs Reversal

White House Press Secretary Karoline Leavitt is getting called out after she attempted to justify President Donald Trump's sudden reversal on his proposed tariffs, telling reporters that his actions make sense because he has a master plan to make the world bend the knee.

Trump declared a full 90-day suspension of all the “reciprocal” tariffs that took effect at midnight April 10—except for those on China—in a dramatic about-face from a president who had long championed his historically high tariff rates as permanent.

Keep ReadingShow less
religion signs
Noah Holm on Unsplash

People Explain What Stopped Them From Going To Church Anymore

There's been a perception of a bit of an exodus from religion for the last several decades. But humanity has gone from no organized religions to oppressive religious regimes to rebellion and back again over the last several millennia.

But is the 21st century when religion finally fails to bounce back?

Keep ReadingShow less