In highschool I asked a girl to come watch a movie rental with me and some friends. She was sitting on the floor in front of me, and rubbed her neck saying that her neck/shoulders were sore. Completely missing the cue to offer a back massage, I got up and offered her a Tylenol. My buddies ribbed me for that for a long time. Somehow with my terrible game I still managed to marry her and we have 3 kids now.

twilling8 , JESHOOTS.com Report

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Watching TV in my living room at roughly 2 a.m., in the dark.

Her: *applying strawberry lip gloss*

Me: Why are you putting on lip gloss?

Her: Strawberry lip gloss tastes so nice.

Me: Haha, you're weird.

Her: Want to taste?

Me: Nah, I already know what it tastes like.

Commence several years of late-night self-loathing and regret.

jamoce4269 , Letticia Massari Report

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While in high school I was at a gig with a bunch of people from my year and had been standing next to this girl the whole night chatting.

Another guy asked us if we were together and she replied 'not yet' and I laughed and replied 'good one' while she looked at me weirdly.

I had such a crush on her as well.

McClernon , Martin Lopez Report

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So my boyfriend is so bad at flirting, we have known each other for 15 years and we were always just friends. We always had secret crushes on each other but we’re always dating other people.

About 6 years ago after we had both been single a while, I had invited him over to go in the hot tub with me. Legit had candels lit and everything, not a move was made. Even after we got out I was sitting with him on the couch I put my head in his lap, he legit went nonverbal.

The next week was new years and when the ball dropped I kissed him and all he could say was ‘you are interested in being more than friends?!’ Lol DUH

That was 5 years ago, now we are getting married next year :)

Skrimppy666 , Tima Miroshnichenko Report

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Sometime back in the early 2000's
Having dinner with some colleagues..


She: Hey r/madasaturtle , Ive never been with a Dutch Guy.......

What I should have said:
"Well, lets do something about that tonight."

What I said instead :
"Me neither "🤦‍♀️

Madasaturtle , Katerina Holmes Report

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I had a girl literally just explicitly say she liked me and wanted to date and I assumed she was joking. She was not.

boparoy485 , August de Richelieu Report

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"Hey, wanted to ask if you are free this weekend?. We can make some pasta and tiramisu together. I'll bring the ingredients".

"Thanks for the offer, I plan on sleeping all day this weekend" 🤦‍♂️

She was an exchange student from Italy.

druranus , Anastasia Shuraeva Report

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I had a girl in university ask if I was single. When I said yes, she asked if I wanted or was looking for a girlfriend and I said yeah I suppose so, and she came back with, 'Yeah, being single is tough, would be nice to just have someone to go on dates with.' I, in all my glory and skills with the ladies, came back with 'yup, sure would be!' And walked into class before her.

mfkterrence , cottonbro studio Report

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I was snapchatting a girl from my high school when there was a pause in her response, then she sent me a post shower selfie with her arm just barely covering her tits with the caption “come play zombies” and my dumb**s goes: “Do you have xbox live?” “No” “Then how will we play?” “Idk” Her shirt was back on after that. It’s been 10 years and i’m still kicking myself.

Comeonjeffrey0193 , Andrea Piacquadio Report

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My brother was once driving a girl home when she said she thought he had a flat tire. She insisted they pull over and check. She directed him onto a narrow road surrounded by trees. He got out, checked it out and said it was fine. He was about to put the car in gear when she said "as long as we're here, let's just hang out a bit." **He asked what she wanted to do. She said "I'm sure you'll think of something" and put her hand on his stomach. He chuckled and said "that tickles"...before removing her hand and adding "come over to my house, you can check out my Xbox!"** Then he put the car in gear and drove home. Anyway, he finally figured it out that same night, when he told me she was "acting funny" and I clued him in. The next day he found her, first thing in the morning, and said "let me give you a ride home, I thought of something for us to do." Not the smoothest line, but it got the job done.

_eviehalboro , https://www.pexels.com/photo/young-diverse-couple-relaxing-after-unpacking-car-while-moving-home-4246265/ Report

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Went on a short road trip with a girl from work. When booking hotels for the stay, she said "Let's book a single room with separate beds; it'll save us money". I thought that was a good idea and went ahead. That evening when we went to bed, I was showing her a YouTube video on my phone and she went "Make yourself comfy! Why are you sitting on the edge of the bed?", and raised the comforter - indicating that I ought to slide in next to her in her bed (which I did). When we were chit chatting, I reached out for a bottle of water that was on a table across from her and accidentally brushed her bra strap with my elbow. I apologized and took a gulp of water. She asked "Is my bra in the way?". I said "Nah, I managed to get the bottle, don't worry about it!". One day after the road trip ended, it hit me. And yes, I know I'm an absolute dumb**s.

haajisquickvanish , Pixabay Report

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In high school, I caught a wickedly beautiful classmate sitting at my desk. When she looked up and saw me, she turned bright red and looked extremely embarrassed. Hours later, I realized that someone had written a love note directly on the cover of my notebook. . . And all I thought was “huh, that’s weird”.

To this day, I think of how stupid I was at 16

InformalManager3359 , https://www.pexels.com/photo/woman-reading-book-inside-a-classroom-8419496/ Report

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A girl I had a crush on sat on my lap because she had white shorts on and didn't want grass stains. She then sighed and said she wished someone would ask her to prom. I assured her that someone would. And it never occurred to me that I had a shot. Years later she punched me for being so oblivious.

enigmaunbound , https://www.pexels.com/photo/a-smiling-woman-sitting-on-the-man-s-lap-5933273/ Report

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We were seeing a movie together and she said she was cold. I said "yeah it's pretty chilly" and did nothing. Later she said it again, pretty obvious what she wanted. I proceeded to give her my jacket to put around her.

I'm a practical man.

hixika8431 , Tima Miroshnichenko Report

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My first weekend of college a girl asked me if I wanted to wrestle her in my dorm.  I wrestled her in my dorm. Nothing more.

Jdw5186 , Tima Miroshnichenko Report

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I either missed them all, or there weren't any to miss to begin with.

Qimmosabe_Man , Mental Health America (MHA) Report

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A year after high school, a girl I'd been crushing on for over a year and knew through mutual friends invited me over her (parents') place to...watch Smallville?...and at one point said her a*s was kinda sore and needed a massage. Proceeded to roll over in her skimpy volleyball shorts and look at me. I nervously gave her like the most clinical and non-sexy butt massage you could imagine. I was nervous and didn't want to seem desperate because this girl was out of this world gorgeous and I just felt very average. She just felt way out of my league and I always thought we were "just friends." To make things worse, that same night, a little later, this one girl from work who had a crush on me called me and I was awkwardly chatting with her trying to end the convo, and girl I was crushing on came in and jumped on my lap and started smiling, laughing, and grinding, knowing it'd make it more awkward for me. Just thought she was being playfully annoying and didn't imagine she might actually like me. Watched Smallville and went home.

A year before this, she asked me to her prom (she went to a different school). And a year or two AFTER all this, she was visiting me and my sister (she was a mutual friend to us both) after we moved to a different state. She stayed over at my place and one evening said that she always had the biggest crush on me and doesn't know why I never reciprocated her advances. She then got up, looked over at me, and walked into her bedroom. I just...assumed she was tired and going to bed. I missed every single opportunity that could ever opportune on God's green earth.

indiana_josh , cottonbro studio Report

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Drove every week from Pennsylvania to Chicago to see a girl I had a crush on. Still lived with her parents, so I never stayed the night.

She always was flirty, but 'then-me' was oblivious. When I stayed later than usual one night, and I yawned, she said, 'You should just stay the night and we can get a hotel room.'

I said, 'Nah, I'm good to drive, I'll make it.' She said, 'No, don't be silly. We can hang out tonight.
I was in the middle of Ohio when I realized what she meant.

mapom66490 , Katerina Holmes Report

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This was back in high school. I was super shy. I had been crushing hard on this girl since freshman year and everybody knew it. She had thrown hints at me forever and I never acted. I was insanely good at math.

So one day as I'm coming out of class she stops me and says that she heard that I'm some kind of math genius and asked me to tutor her. I asked her what she's going to pay me. She says very suggestively "oh don't worry, you'll be well rewarded".

My stupid a*s responds, no I need actual numbers to know if it's worth my time smh. I was so dumb lol.

threat024 , Jeswin Thomas Report

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Back when I was a teenager…

I was with a girl, in her bedroom, alone late at night. She was lying on the bed looking at me, telling me how handsome I was and how much she liked my eyes.

I said thank you, and that it was late, and that I should get going. To this day I cannot explain my actions because this girl was absolutely gorgeous and I had crushed on her for years. She was my friends younger sister. I think my brain just short-circuited and refused to believe that she was telling me the truth, and I was so nervous that I had no idea what to do. It hurts to think about.

tenaciousDaniel , Alex Green Report

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A girl legitimately said to me "take me home" as we parted ways.

I thought she was joking.

Judging by the fact we had just finished kissing eachother (passionately) only a few minutes beforehand I think it's safe to say she wasn't.

#brainonairplanemode

anon , Jonathan Borba Report

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Met 2 girls at the club and we hit it off. After like 30min one of em says “wanna come with us to the car? We need to change?” What I said?! “Nah you guys look good.”

Didn’t know anything was amiss until like 3mo later. I shot upright outta bed and realized my mistake.

disphugginflip , Edoardo Tommasini Report

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"'You know I'm single right?'

'Yeah, me too.'"

boparoy485 , cottonbro studio Report

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After a photo session with a close friend, she said I can stay the night when I said I'm tired.
I obliged, thinking it's just a nice offer.

During the night I woke up slightly because she had grabbed my hand, put it on her hip and pressed her butt against me.
I was still groggy and didn't think much of it and went back to sleep.

In the morning she turned around to face me, got her face so close her nose was touching mine... And again, I went back to sleep.

krtshv , anait film Report

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Had a friend at University who was a best friend, except that I was too dumb to see that I was more than a friend to her.
She was smart, beautiful, funny, very patient and we gelled straight away.

We always went to parties together, spent the evening with different people circulating, had different partners over the years, but she would always insist I saw her home safely and of course I just kept on missing those obvious signs.
Roll on three years and everyone is going their different ways and we go out for one last night for a drink, have a great time and I see her home as usual except this time she doesn't hold back and basically drags me into her bedroom.


Honestly I was so shocked, so dumbfounded that my 'best friend' who happened to be female fancied the a*s off me that it totally wrong footed me and we literally couldn't do anything apart from collapse into a fit of giggles and fall asleep in each others arms.


I never saw her again but every now and then I think back to that time and wonder what if I wasn't such a dumb-a*s, would it have failed, would it have been amazing and life happy ever after?


Who knows apart from in an alternative universe.

Common-Ad6470 , Polina Tankilevitch Report

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Dropping her off at her house after a joint college project

"My roommates and I have a wager over who can get laid first."

Awkward pause.

"Well, good luck with that I hope you win" *drives away.

BoardGames277 , MART PRODUCTION Report

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In class, a girl asked if we could study together for a minor quiz at her place.

A friend overhears and asks if he can join us, I say yes immediately before she can say anything.

She sends us her address and a time. I show up and she answers the door in a bikini. Nobody else at her place. She says she was sunbathing and asks me into her room while she changes. I look away to be polite and then make small talk once she's done.
My friend shows up 30 minutes later, turns out she told him that the study group started 30 minutes after what she told me.

Sigh...

mapom66490 , Mikhail Nilov Report

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Woman I'd been friends with for a year or two, "I bet you have a beautiful c**k ;)"

Me: "It's alright, keeps me entertained, lol." Then I asked a question about Chinese food.

Couple months after we lost contact, "Ohh... OH... damn"

Xenovitz , https://www.pexels.com/photo/man-eating-noodles-7594054/ Report

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Woman: "Would you want to go for a coffee.... At MY place... (at 2 am after a party)"....


Yeah still hate myself for it.

TheKinkyGuy , PNW Production Report

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I have very flexible joints. As a result, I was well known for doing tricks with my hands during my early uni days. Things like bending my fingers backwards to touch the back of my hand, touching my arm with my thumb, bending fingers into a Z shape etc.

I was at a party with classmates and this girl I vaguely knew asked me for a private demonstration of my hands. I was slightly buzzed at the time so I said sure and took her to the kitchen while she giggled. I started doing my usual tricks but I quickly noticed something was wrong because she got this disappointed look on her face. She mumbled something akin to "ok cool" and left the party claiming she was tired, leaving me confused for the rest of the night.

It took me 3 days of sobering up before I realized I had f****d up and by the time I saw her again it was too awkward to talk about.

Ralath1n , RDNE Stock project Report

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