Not that I'm proud, but I've got you both beat...
When I was 17 creeping up on 18 I got my first real job at a hospital parking garage. The first day during lunch I decided to go to this java cafe inside of the hospital, and when I got there I was confronted with the sexiest girl I had ever seen in person (think: an 18 year old Eva Mendez), and actually chocked up a bit when I tried to order. I remember actually thinking to myself on the way back to the job that day, "never going to happen in a million years -- just forget about it."
Then that same day after work I sat at the bus stop waiting for my bus ride home, and then here she comes. She sits down at the bus stop right next to me, and then like some shit out of a movie just starts talking to me and opening up to me big time. It isn't long before she's dragging me to this coffee shop across the street and buying me espresso shots as we got to know each other fairly well. I was still in shock at this point, and couldn't believe any of it. She was a real life
Manic Pixie Dream Girl, I shit you not.
Anywho, long story short, she informs me that she's emancipated and has her own place and that I should come over. I make some bullshit excuse as to why I can't come, but we exchange numbers and plan it for another day.
"Another day" comes, she not only wants me to come over but says she wants to cook for me as well. This time I say something extra lame like, "oh I wish I could but my mom needs me at home today." So postpone it yet another day. "Yet another day" comes and she calls me up, eventually telling me how horny she is and how she
needs me to come over. Even though it's one bus ride away, I chicken out again. After that she stopped trying, probably figuring, with good reason, that I wasn't interested in her.
What blows my mind about this is that I was no virgin, it's just my few girlfriends before that were nowhere near as hot as this girl and I felt like I had to live up to some Godlike expectations sexually to please her, and didn't want to fail or some shit. So basically: I was an insecure little bitch. It pisses me off because had that been just two years later when I entered into college and got a whole new perspective on life I would have gone for it without a care in the world.
tl;dr -- I cock blocked myself out of potentially the best sex of my life multiple times with the same smoking hot girl who was trying hard to jump my bones.
Nice to know I'm not alone in these kind of situations.
When I was 15 or 16 years old I developed a crush on this alternative blond girl in my class.
She tended to go out with older guys and prefered the rough guys.
I was at the time a bit of a loner. I've lost a brother who was very dear to me and tended to throw myself in schoolwork, drawing and metal-music. I tried working on my people skills and slowly got closer to her.
Especially in our last year. She chose to sit in my proximity in class, when tasks were handed out she made sure she wound up with me as a partner and we hung out a lot.
She sometimes leaned over in class, whispering information like her favourite body parts and other spicey information... everyone else saw what was happening except of course... me.
Now at the end of the year, after graduation we held a couple of parties.
At one point we're standing outside (I had to leave the party because I felt a bit depressed).
She comes up to me and comforts me... then she whispers "it's cold out here" in my ear.
I react "well better get inside then"... (stupid fuck)... she gets drunk - I get drunk because I still had the feeling it wasn't going anywhere... and after a while we all leave.
Now we go of to college (university) and we don't see each other for about a year. This was the time before e-mail and mobile phones mind you, so keeping contact wasn't easy. I got a new group of friends and some fleeting relationships (she was still permanently on my mind though).
At a party of a mutual friend we meet again.
We get to talking and I think to myself "this is my last chance, go for it"
I'm taking it easy... at one point she asks me if I've seen anyone from highschool in the last year. I think this is the moment to tell her what's on my hart for so many years.
So I say: "No, and frankly there's only one person I would like to see regularly and that's you..."
To my amazement she starts crying, she says "don't say that to me, not now, I can't take this..." and runs away.
I sit there in shock... what's happening here? I decide to go after her, but she's gone...
And then it dawns on me... all those years wasted... how could I've been so blind. Everything fell in place and I could kick myself for not seeing it.
I only saw her again two years later, I was already together with my wife (who's practically perfect in every way might I add), so for me the chapter was closed.
Still I sometimes wonder what could've been...
When I look back at my youth, I must've been a real retard when it comes down to me and the ladies. I have to other friends who recently told me they had a major crush on me in my first college years and that they really tried to convey the message but I wasn't interested.
I think one obstacle was the fact I was convinced I didn't have any chance with that kind of women anyway.