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People Divulge The Most Unexpected Person They've Hooked Up With

Man watching as woman walks into bedroom
Photo by We-Vibe Toys on Unsplash

Reddit user Fickle-Computer-6883 asked: "Who is the most unexpected person you had sex with ?"

Life is like a box of chocolates; you never know what you're going to get!

Every day can be full of surprises, especially if you're willing to explore, take chances, and try new things.


And sometimes chance encounters can definitely turn into something... more.

Curious, Redditor Fickle-Computer-6883 asked:

"Who is the most unexpected person you had sex with?"


A New Form Of Communication

"My friend’s housemate’s friend, who didn’t speak a word of English. I smiled at her during a house party, then about two hours later, she grabbed my hand and led me into the spare bedroom."

- Active-Strawberry-37

"Same thing happened to me with an Italian girl. We met earlier, and later she grabbed my hand, put her index finger up to my mouth, and said, 'shush,' and proceeded to lead me to her bedroom."

- floppybunny26

Healing The Inner Teen

"I had the biggest crush on this girl in high school, but we never had a conversation beyond random pleasantries since we were in completely different social groups."

"Fast forward a few years after graduation, I was going to Australia for a while, and a friend told me about this girl from our high school who was apparently living there now. So I randomly hit her up on Instagram, seeing if she’d like to meet up at all."

"I ended up spending the entire month with her, and we were hooking up pretty much the entire time."

"17-year-old me would be so proud of 25-year-old me."

- whiskeynise

'Lord Of The Rings'... Marathon?

"I was a nerdy 18-year-old who had only been with one girl. A girl I had just graduated with started a tattoo apprenticeship, and I commented on her Facebook post, congratulating her."

"She randomly DMed me a few days later and asked if I wanted to maybe watch 'Lord of the Rings' with her. H**l yeah, I wanted to watch 'Lord of the Rings.'"

"So she came over to my place, and before I realized what was happening, we were making out. I just wanted to watch my favorite movie and instead had the best sex ever with an almost stranger."

"Situation ended up with me having a ferret, a urinary tract infection, and a bad tattoo in a noticeable spot."

- 20somethingmokid

The World's Best Cup Of Coffee

"A waitress after her shift ended. I had never met or even spoken to her prior to her serving me black coffee at like 11:00 PM."

- mmmhmmfriedtaters

"Similar story with a flight attendant. I had an overnight layover; she rolled past me leaving the airport and asked me when I was leaving. I told her in seven hours."

"She said, 'Well, the flight agency booked my room here, so stay with me.' I played it cool as we went to her room, I didn't know if she meant on the fold-out couch or something."

"...It didn't mean the fold-out couch."

- arlenroy

An Unexpected Line

"My all-time college crush. We spent hours talking at a bar, just me and her."

"Her friend came up asking if she wanted a ride home with her. My crush said, 'No, we’re gonna go back to my house.'"

"My jaw dropped so low, it was a ridiculous move. But so hot."

- stenny21

Not Like The Videos

"Years ago, I worked for a fairly high-end men's formalwear clothier. Every year, we at the management level would fly to California for a few days of conferences."

"Also in attendance one year was the guy who did the voice-over for our training videos. I'd never seen or met this guy, and he had the most godawful monotonous voice ever, perfect for corporate training videos. On the last night, there was always a drink-fest."

"I caught glances with this really cute guy and started chatting, it turned out to be him. He took me back to his room. There wasn't anything boring about what followed, and I never looked at training videos the same way again after that, lol."

- _MyCatsNameIsBinx_

"It would have been hilarious if he used the training video voice back in the room."

- NYArtFan1

Be Careful What You Wish For

"A neighbor chick who’s boyfriend stormed off one day because for some reason he thought she’d been f*cking me. Up to that day, I’d never done anything more than exchange pleasantries in passing with her."

"After he split, she came over to apologize for his behavior (I had overheard the argument) and introduce herself. Next thing I know, I’m waking up in her big soft bed after an all-night romp."

- Cheap-Bell-4329

"That boyfriend is a really powerful manifestor."

- Schlag96

The Beginning Of Something Great

"My wife, though not wife at the time."

"We were at best acquainted work colleagues."

"We were out at a work function, and I was interested. I didn't even do anything to pick her up, I just danced with her for a while and then told her I'd like to see her sometime."

"To which she pretty much said. 'Okay, let's go,' and about half an hour later was having what was the best sex of my life."

"We've now been together almost 20 years."

- Kayback2

An Excellent Wine

"This hot manager at my company. She sat a couple of desks away from me and wasn't on my team, but we'd made eye contact a couple of times. Anyway, I go out drinking with my friends one night, and after I'm a few beers down, I head to the john to relieve myself."

"On the way back, guess who I see downing tequila shots at the bar. The liquor in my bloodstream emboldened me with the confidence to approach and greet her. She was pretty drunk, too, because she sprang up and hugged me."

"She admitted that she was pretty depressed after this guy she was seeing just vanished into thin air. After talking for god knows how long, she says, 'By the way, I have this really good Chinese wine back at my place. Wanna check it out?'"

" We head back to her place, and no sooner than the door is latched do we start furiously making out and taking each other's clothes off."

- _betterpingfring

Not A Good Look

"My probation officer."

- Wrong-Pizza-7184

"Pretty sure that's a crime."

- WhoIsYerWand

"Oh yeah, that's a felony in my state."

- Foijer

High School Reunion

"Girl from high school. She was considered one of the hottest girls in our school, easily. Unobtainable queen bee. Not in a mean way luckily she was actually super nice."

"Shortly after graduating, maybe a year or two, we ended up hanging out through a mutual friend. We found out we had a lot in common, and we very quickly went from friends to friends with benefits for one amazing summer before parting ways amicably."

"That girl was my sexual awakening, too. She was down to do anything, anytime, anywhere, with enthusiasm. I still look back on that time with great fondness, and I hope she's doing well."

- Idontdanceforfun

Art Imitating Life, Or...

"A girl who was sitting next to me on a plane. She was drawing, and I watched three of the flight attendants comment on how beautiful the drawing was, so I made a joke about the odds of another person walking by and saying the same thing."

"We chatted for a while, and we happened to be flying to the same city (no connecting flights or anything); it turned out we both lived there but in opposite parts. As we were getting off the plane, I asked if she would want to show me around the city sometime, and to my surprise, she said yes! We hung out probably about a dozen times, and had sex every time. We did not do it on the plane, though."

- RicardoVonCoucho

Do Not Recommend

"Someone who I absolutely used to hate as a teen. A few years back, when I was 26, I had sex with her after a party she attended (mutual friends thing) after not seeing her since high school."

"The next day we hung out for a bit, and I was reminded why I couldn't stand her."

- RipAgile1088

Happily Ever After

"At my 50th high school reunion, I re-met our Homecoming Queen. We hadn't been close in high school (she was way out of my league), but got along great 50 years later. We're now in a long-distance relationship, travel together, and visit back and forth. We're a couple of 70-year-old rabbits..."

- thirtyfivesteps

"I was at a wedding a few years ago for an elderly couple, in their 80s. They had grown up together, actually dated in high school, and then he joined the army, and she got married."

"They randomly ran into each other after both their spouses had passed away, in their 80s. Turns out, they had always thought of the other as "the one that got away,' and they got a second chance."

- Jeddak_of_Thark

Unexpected Turn Of Events

"A coworker I never liked. We were forced to work together once. Turns out she is really nice to work with and talk to. One thing led to another, and now we’ve been together for 13 years now."

- CJLogix


Most of these stories were pretty surprising, either in how they happened or in how quickly a situation escalated. It was adorable to see how many of these accidental encounters turned into something more, from meaningful marriages to long-time marriages.

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