What's the embarrassing thing you did that still makes you cringe when you remember it years later?

it was the end of summer 2001, and i was 16 years old. the girl of my dreams would be moving to england the next day. that whole summer i had been working up the courage to tell her how i felt, but never did (this sort of thing was not my strong suit back then).

so after pumping myself up drinking some stolen vodka (my first experience with hard liquor) with Fuel and Lifehouse songs playing in the background (we had gone to a show their show last winter), i put on the popeye t-shirt she had inexplicably thought was a good birthday present, stole my mom's cellphone, and took off on my bike.

the ride over there was about 9 miles, and it took me 3 hours. no, it was actually probably around 45 minutes, but it felt like forever. at this point it was about 9:30 at night: not obscenely late, but not the best time for unannounced visitors.

why hadn't i called her and asked if it would be okay to come by? well, there were 2 things about her that i knew to be true: she was much more reasonable than myself, and she was almost certainly not in love with me. if i had called, the gravity of the situation would have been totally lost on her, and i would miss my big chance.

so i pull up at roughly 9:30, completely oblivious to the existence of murphy's law. i wonder now how much better my plan would have been had i known to account for everything that could possibly go wrong. but account i did not, and go wrong everything most certainly did.

her family was wealthy, and they lived in a big house in a sparsely populated area of town. their neck of the woods had beautiful houses, a low crime rate, and several other wonderful things. what it lacked, however, was cell phone service. shit. shit, shit, shit.

i've come this far, i'm not turning around now. maybe her parents are asleep. maybe i can gently knock and she'll be the only one who hears it. i knock, but there's no answer. i'm afraid to knock any louder. the doorbell is out of the question, because it's an intercom system that rings throughout the house.

i sneak around to the side door and try to see if i can see her through the window. i see nothing, but then i hear "tess! tess! jack's here!" fuck, fuck, fuck, fuck, fuck. it was her younger sister. i've been seen. "what? what are you talking about? no he's not." shit, shit, shit, shit, shit. "he is! he's at the side door!" this is not going to end well for me.

she comes to the door. "jack, what's going on? you're wearing popeye, and you rode your bike?" thankfully she wasn't scared or angry (both perfectly appropriate reactions with the way this must look). she was confused. meanwhile i was drunk enough that i couldn't come up with a single thing good thing to say, but sober enough to know that it was certainly best that i don't even try.

"i'm uh, i'm uhhh, i dunno. i'm sorry. this was a bad idea." her parents come to the door in an equally puzzled state. they have me call my mom to come pick me up. tess and i then sit by the tv in terrible awkward silence until my mom arrives. "i'm sorry" i tell her again. until today, i hadn't thought of her in years.

/r/AskReddit Thread