27 Men Confess The Times They Were Completely Clueless To A Girl’s Flirting


I was on a plane ride back from vacation one year when I was 16-ish. I went to the front of the plane to use the restroom and as I’m walking back to my seat, this girl hands me a piece of paper and goes, “You dropped this.”

I’m one hundred percent confident that I didn’t have any paper in my pocket beforehand, so I politely say, “No, I didn’t, but thank you.”

“Yes. You did. You dropped this,” she says firmly.

At this point, I’m irritated that this girl clearly doesn’t realize that I’m more aware of the contents of my pockets than she is, so I tell her once again, in front of increasingly bewildered passengers, that I did not drop any paper.

Her mom (I assume) laughs, and the poor girl, exasperated at this point, says “Just take the paper!” So I say, “Fine!” And return to my seat, where my parents laugh at me while I open the paper with her phone number on it and realize I’m the dumbest person I will ever meet.



She showed me her nipple piercing, by removing her entire shirt and bra.

I said, looks nice.

She said, did you get a close look?

I said, yup they did a good job.

Shirt went back on.



Years ago I was crushing on this girl HARD, for months. She worked for the same company I did, but in different building, so we rarely had the opportunity to interact. We’d probably only spoken a couple of times in passing.

Well, a few days before Christmas one year, she comes waltzing up to me unexpectedly at work, wearing one of those party headbands with a springy plastic mistletoe bouncing around over her head. Says something like, “Hey, whats up. Like my hat?”

“Uh…yeah, cute,” I say.

“It’s mistletoe…,” she says, with a big shaky grin. “People have been trying to kiss me, can you believe it!”

My dumbass responds with. “Yeah. That sound’s pretty inappropriate,” like I’m damn Dwight Shrute from The Officeor something.

She says, “Oh, ok” and hightails it out of the building without looking at another person.

At the time I was a little heartbroken that the girl I thought I liked was the type to just randomly go around asking coworkers to kiss her, and I resented being lumped in with them (arrogance). Didn’t occur to me until later that I was probably the only person she approached. Shit, she probably went out and got the silly hat specifically to set up that scenario with me because it was clear that I didn’t have the balls to make the first move beyond giving her puppy-dog eyes for half a year. The way she shuffled away was like someone punched in the gut.




I had a girl ask me once if I wanted to sleep with her. It was nearly a year later that it occurred to me that she might have been serious.



Honestly, girls being forward is even more confusing than girls giving hints. I’ve had a conversation like this more times than I would like to admit (two. I’ve had it two times)

Me: I’m bored, what do you wanna do?

Her: we could have sex

Me: haha very funny. Grand theft auto?



I used to flirt with one of the female bartenders at a bar I worked at. It was really fun and there were so many signs.

The biggest one that I should have obviously taken was when we left work at about 4am and I tried tickling her. No reaction and then she says:

“I’m only ticklish in one place.”

She then began to rub her inner thighs near her lady parts. Basically giving me permission to go in and “tickle” her.

I laughed and said:

“Oooo now I know how to torture you with tickles. I’ll get you next shift.”

Drove home. On the way home wow did I realise what just happened. She did not like the denial and that door was closed forever. :(



Was watching a movie together on a couch and she went to lay her head on my lap. I got up to get her a pillow and blanket and set her up on the other end of the couch.

In my defense it was the first time watching The Matrix.



A girl once said to me “did you know that if people look you a lot in the eyes, it means that they either want to kiss or kill you?” and then she stared me down. I was very confused about why she would want to kill me if she had spend so much time talking with me.



Her: want to share a taxi back to my place?

Me: sure I can drop you off then go home myself.

Woke up in the middle of that night and knew exactly what I’d done.



High school, 9th grade (aka freshman year). Super hot girl, my friend, and me are hanging out. We go back to her place because nobody is home. After a little bit, my friend says he has to go home and leaves. Me and hot girl are sitting on couch watching some crap on TV. She turns to me and says “wanna see my new swimsuit?” I thought for sure she meant she was going to go get it, bring it back, and hold it out to show it to me. That didn’t sound interesting to me, so I said “no thanks.” A little while later I left. Realized what happened about 5 years later.

Another time, I’m 22. Playing on a recreational sports team. I would usually drive this one girl on our team home afterwards. On one of the drives, I mentioned that my hands were cold (it was winter). She says “when my hands are cold, I usually put them between my legs… it’s always warm down there.” I thought about this for a moment, and concluded that my pants were too thick to meaningfully warm my hands. “I’ll just put on some gloves, I guess.” Thought nothing of it for years. A couple weeks later she tried again with “Do you have a girlfriend?”


“I can help you with that ;)”

She got through to me that time.



Went to see a band with a girl in my teen years, she invited me to stay at her place afterwards. She then told me I could sleep in her bed, then she got undressed.

I went to sleep fully clothed and oblivious.



My best friend and I are talking on the phone.

We spend a couple of hours that day talking about stuff that turns us on, and her various sex toys. One of the things for her is the smell of cooking garlic.

She then tells me she’s cooking something with garlic in it. She eats whatever it is, making yummy noises while we’re still on the phone.

She then tells me she’s going to get undressed and take a shower. She went out of her way to tell me she was leaving the front door unlocked.

I said ok, talk to you later, and hung up the phone.



First weekend studying abroad, it’s the end of one of the best nights of my life, and myself and a girl from the program are wondering around trying to get one more beer before packing it in. Walking down a quiet side street she starts talking about how tall I am (a topic i am very used to) and she confesses “I’ve never kissed somebody as tall as you.” My response, “huh, I guess neither have I.” I didn’t realize until two weeks later when we took a weekend trip together that she had any kind of feelings for me. That was an awkward trip.



We took anatomy and biology in college. We used to study together. I mentioned that I had an inguinal hernia that I was having surgery on in a few weeks.

She asked to see. I explained that it was right down beside my scrotum. She said she didn’t care, and was curious to see what it looked/felt like.

I undid my pants and pulled my underwear aside enough that she could see. She reached in and cupped my balls and had me cough so she could feel the effect. She palpated around my junk feeling the hernia.

The whole time I was concentrating very hard on other things, I assumed this was a “professional” curiosity.

Okay, you’re thinking. She could’ve just been a curious, and wanted nothing more.

Then she asked if it got better or worse during a BJ. I replied that I hadn’t been lucky enough to have my condition and a girlfriend simultaneously.

She replied that I didn’t need a girlfriend, just the right girl, all while gently cupping my scrotum.

I looked at her, buttoned up, and said something about wishing I could find that person.



I was 17, and not worldly-wise. Went back to her halls (dorm) fairly late at night. I was examining her CDs (it was the nineties, this was one of the ways you assessed if someone was okay) and turned back round to find her sat on her bed in her underwear.

I said “Oh, sorry, you need to go to bed?”, and left.

About two years later I was walking down the street when it finally clicked.



A girl (my crush at the time) and I were at my cabin alone for a night and all of our friends were coming out the next day. When we first arrived she said, “I call that bed” and I told her, “But that’s my bed” she then jokingly said, “Well then I guess we’re sleeping together.”

Sure enough, she throws her pillow on my bed and lays down. I then lay down beside her on my side away from her (I was incredibly awkward and uncomfortable about the whole thing). I can hear her moving and shuffling and then I twitch my leg a little bit and touched her leg, she had gotten very close to me, I immediately apologized and moved closer to the edge of the bed. I felt like she was just messing with me because she knew I liked her.

About 3 years later she told me she kinda wanted to mess around with me but thought I didn’t want to.

Fuck. Me.



On two separate occasions, girls have bought me drinks at the bar. And on both occasions, my dumb brain gets me to say “oh thanks!” then proceed to take the drinks and walk off…



She complained about how long it had been since she’d been eaten out.

It was 15 years ago and the memory still makes me cringe. I friendzoned my damn self.



I was 22 and working as a cashier at Target. I rang out a VERY beautiful older woman. I scan her items, pitch a RedCard, all the usual jazz. After I give her the receipt, I turn around to restock bags. When I turn back, she hands me the receipt, smiles, and walks away.

I look at the receipt and she has written her phone number. Immediately, I yell “Why did you write your phone number?” She comes back, takes the receipt, crumbles it up and says “If you have to ask, you’re not ready.” Walks away.

I explained to one of my co-workers, and he hit me.



We were at my house studying for an organic chemistry exam. Both of us were sitting close at the table with my laptop in front. I was talking her through the mechanisms and such, and she would lean on me and lay her head on my shoulder. As I kept going, she wrapped her arms on mine as I kept blabbering on. I thought I was massively friend-zoned, which is why I didn’t think much of it.

We took a break to watch a movie and she suggested we spooned on the couch. “I’m so friend-zoned that she’s comfortable spooning with me” I thought to myself. She probably grew impatient that I wasn’t picking up the signs, so out of nowhere, she does a 180 and starts making out with me. Been together for 2 years now.



Went to a party, was hitting it off with a girl I knew through some social circles. She was cute and a ton of fun, but I had to take off after a few hours.

The party was in a friends apartment in the same building I lived in at the time. She was following me out, saying she needed to leave as well. We both called the elevator, and just kept small talk/flirting going on in the elevator.

I got to my floor, and she said that she thinks she forgot her jacket at my apartment. At this point I didn’t catch what was going on, so I told her that she’s never been to my apartment.

I only realized what the hell was going on after the elevator doors closed.



Cute girl in college sent me an IM (I’m old) that she heard I had a cool room and wanted to see it.

I looked around at my Pier One decorations with pride and sent her a picture.




I was at a bar last weekend.

Closing hours came around and the bartender asked us to drink up and get going. So she downs the rest of her beer, and i ask.

“And how did that taste”

She answered, “Why dont you come find out”.

I just thought to myself, well you already drank it all, and left. I am not a smart man.



Watching a movie at her place on her couch..she put her feet in my lap.. I moved them off because her heels were slowly rubbing my dick and balls and it was uncomfortable.

I remember her sighing very loudly…



A girl once told me that out of all the guys she knows I would be the only one she would date and I responded saying “sweet.”



We were just chatting on the he phone and she said “we should go see a movie sometime”

Me: I’m not a big movie guy.

Her father owned an oil company



Was laying with a girl I liked. She told me that it was “cold in here.” Instead of taking the cue and cuddling with her, my oblivious ass says, “well, I can go check the thermostat!” She sighed and said, “no, it’s okay.” I didn’t realize my incompetence until at least a week after.

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