“We were stargazing.
Him: OK, to find a shooting star, just look at a point that you’re attracted to.
I look straight at him.
Him: No you need to look at the sky!”
-lulumustelidaeee
“In year 11th I liked this guy and I had been dropping hints for a while and since they weren’t getting me anywhere I (with a lot of encouragement from my best friend, who was convinced he liked me too) outright told him “I like you”.
His answer hurt a little not gonna lie “What? That wasn’t even funny”
And as it turns out my best friend was terribly wrong because his answer was “well this is awkward, I actually like your best friend”.
-RogueX000
“Asking for his hand, then writing my phone number on it. Still didn’t get it.”
-BB12889
“Straight up sitting on his lap when watching a movie, kissing his cheek, and nuzzling my head into his neck + multiple other obvious verbal and physical clues, but he thought I gave off mixed signals and only wanted to be friends?”
-Themadbelle
“This is so dorky but I liked a boy in high school and he was nice and we’d talk on aim a lot and one day thinking I was being SO brave I wrote him “I’ve been locked inside your heart-shaped box for weeks” lmao I thought it was so cute and he was all “Aw, get out!” Hahahaha if it wasn’t me I’d make fun of me for that”
-madamevulgar
“Oh my, my poor guy. I had been flirting hard core for years, complimenting him, comparing hand sizes, suggesting he needed someone to keep his bed warm.
Doing everything to be alone with him but I think the biggest one was once after a Pathfinder game he said it was time to go home and I said your place or mine. To which I got “I’m heading to my place” I was so frustrated I literally grabbed him and asked him out. Now I wake up every day next to the best man I’ve ever known.”
-velcromidway
“Before my girlfriend was my girlfriend she was just a friend I had a crush on who texted me saying she f@#ked up cause she drunk texted her crush the night before. I replied with “damn, was it bad?” And had a conversation with her.
Some 20 minutes later I realized she spent the whole night in question texting me. I’m not an extremely intelligent man.”
-Sabrowsky
“I think you are cute. Wanna go to the movies?”
He was pretty shocked when I kissed him. We’ve been together for 2 and a half years now.”
-the_better_boobytrap
“When I was in highschool, I had really low self esteem in terms of dating. It was totally mind blowing a girl would even be interested in me. That being said, I was talking to a girl I was interested in and she eventually sent me nudes. I had so little experience being friends with girls I assumed it was a standard friendly gesture that girls do for their guy friends. I wish I was joking about this.”
-jbear876
“Male massage therapist here…. At the time of my stupidity I was 21-22 ish. A long time family friend, from another state came to stay at my parents house to visit our state for awhile.. This girl is gorgeous, I was always attracted to her when I was a kid. Anyways, she has a jacked up back from post military life. She asks for a massage. Massage ends. I step out of the room for her to change. She put a towel on. Comes to the door… opens it. And asks if I want to come in and cuddle for a bit… Years later still regret not taking up her offer.”
-liveyourpotential
“Guy here, I told a girl on MSN years ago that I had a crush on her, she replied, “It’s mutual” and I didn’t know what that meant so I ghosted her.”
-sixesand7s
“Dropping a girl off after dinner.
Her: “you wanna come up for coffee?”
Him: “Oh I can’t drink coffee this late, it’ll keep me up”
Her: “Okay, well goodnight”
-abramcpg
“I asked him out and he replied “Just the two of us?”
-thewall9
“obligatory i’m a guy(sorry), and i’ve had pretty low self esteem for most of my life. one time my friend, a girl i liked, told me i could touch her anywhere i wanted to. i sorta wrapped my arm around her waist in a friendly side-hug sort of way, and she immediately smiled, grabbed my other hand and put it on her boob. i was like “…oh. cool””
-AV8ORboi
“I am a guy but I missed an obvious sign once. Me and a friend were waiting for a few others to show up and they called saying they would be an hour late because they ran down to the university to pick up a buddy. My female friend turned to me and said “well I’ll just have to sit on your face until they get here”. I replied that it probably wouldn’t be comfortable. It clicked in about 2 minutes later and I was lucky she was far nicer than I am smart.”
-Epoxycure
“Would you ever consider dating an older woman?” (I’m 2 years older). He said no so I dropped it of course. Later he asked me out and I asked him about not dating older women and he said that he thought I was talking about my friend, that his friend had to point out that I was talking about myself and then he felt like an idiot, lol.
-mouse361
“I asked him out on a date. He said he was busy, “But hey, my twin is free. Duncan can grab ice cream with you.”
Duncan I got ice cream. I f@#ked off that crush pretty quick. Still all friends though.”
-SalemScout
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