What’s the biggest hint you’ve ever missed from a woman?

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 dumbass.

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

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” (she had mentioned playing nazi zombies earlier in the convo) and my dumbass 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.

“You know I’m single right?”

“Yeah,me too.”

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

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 fucked up and by the time I saw her again it was too awkward to talk about.

Drove every week from PA 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.

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.

A lifetime ago in high school the extremely cute exchange student from Spain sort of cornered me and started asking questions about an upcoming school dance. What is it like? Is it fun? Are you going with anyone?

Ynez, if you’re out there, I’m sorry. I’m a dope.

Watching TV in my living room at roughly 2am, 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 youre weird

Her: want to taste?

Me: nah I already know what it tastes like

Commence several years of late night self loathing and regret

She said, “I do tarot cards. Just before I came here, I did a reading and it said my night would end with a bang.”

…yup.

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…

Hanging out with a coworker at her apartment, each 19/20ish. Sitting on the couch side by side, she complained that her large breasts were a pain to deal with because of their size, followed by”…do you want to touch them?”

I sort of half-juggled them (as though I was comparing the weight involved) and said “hmm, nice.”

Not the only signal I missed that night, but probably my defining moment of obvious failure.

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 ass responds, no I need actual numbers to know if it’s worth my time smh. I was so dumb lol.

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.

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.

They say guys always are just thinking about sex, but boy has this thread proven that wrong

In my junior year of high school I was a teachers assistant for a 12th grade AP English course, and sat near this gorgeous, smart, and really nice girl. We talked a lot and I liked her but always just thought she was way out of my league.

About a week after our prom that year I was telling the teacher about how crappy it was because my date kinda ditched me. He said “well why didn’t you ask ____?” When I told him how I never considered it he laughed at me and was like “Man, you’ve been missing a lot of easy signals. Don’t worry, you’ll get there.”

Apparently being oblivious was my strong suit.

Edit: Probably should have added that she graduated shortly after and I never had the chance to ask her out, etc.

A girl I’d been chatting with for a while asked to come back to my hotel room to see my music collection on my laptop.

So I took her back and showed her my music collection for 30 minutes. That’s not a euphemism, I literally did that until she took pity on how clueless I was and basically jumped me.

Me: “I really wanna try to sleep with a tall girl, see how it’s like.”

Attractive Girl: “Well, I’m 6 feet 2” (I’m about 5 feet 8)

Me: “Nah, I was thinking about 7 feet tall”

Still haunts me.