That would be not asking out a girl i liked in college – the only girl i liked in college – when i damned well knew she would’ve said yes.
How could this ever be seen as a good idea? Well, it was 2 months before she graduated. I figured it was good not to get attached. I’m still banging my head against the wall over this one.
There could be some others, but nothing else comes close.
My birthday last February was one of the worst days of my life. I regret waking up that morning.
No, beagles just hang out eat food, and crap on your carpets, they don’t work.
Going to a football game that I’d been looking forward to for months. I never even saw the game. 
Shooting bottle rockets out the basement window (open).
During those blissful early teenage years, before you have learned that “what” and “if” can be used alongside each other in a sentence. Things progressed well until we got to the “screamers” (the larger whistling bottle rockets). A minor miscalculation in aim sent the bottle rocket careening about the basement den, to lodge beneath the sofa. This was good 
and this was bad :(. The sofa protected anyone from being injured when the bottle rocket exploded, but also trapped the rocket against the carpet. It took a year or so for the hole burned in the carpet to be noticed.
Looks like I sacrificed clarity for brevity. To explain: a potato is a folk remedy for a burn. Keeps the skin moist. For a burn on the finger, one would core out the potato and place it over the afflicted digit.
Watching a morose-looking guy wnder around with a potato on his finger for a day or two was the piece de resistance of the whole episode.
Giving a vague, noncomittal answer when someone I knew in grad school asked me to help her move to Auburn, Alabama. Six months later, when the time rolled around, I still hadn’t come up with a plausible excuse to back out, and the rest is indelibly marked in my brain. I posted the whole extended saga some time back to deafening silence.
Having two Black Bushes straight up on top of at least six Irish Cannonballs (a Black and Tan with a full shot of Jameson’s spooned in between the Harp and Guiness). Only night of my drinking career about which I have no recollection at all of some parts – I have the body mass to cope with fair amount of booze, it was spread out over several hours, I’d had a big dinner and I was on top of my game in those days. They tell me I screamed at the poor schmuck with the guitar until he finally sang “Finnegan’s Wake” to shut me up. I remember the trips to the bathroom to bark at the plumbing after I got home (I thought I made it, until I stepped in the evidence to the contrary the next morning on a similar errand). I definitely remember the dry heaves at precise half hour intervals (at :00 and :30) for two and half hours the next morning, as well as the phone call from my mom a little later to tell me my step-grandfather had died during the night.
I once thought it would be funny and romantic to jump onto the hood of my girlfriend’s car and beg her to stay as she was trying to drive away. Later that evening as the nurse was picking gravel out of my skull in the ER, I realized what a moronic idea it was.
It’s spelled “Turpentine”, dearie. Sorry, I usually don’t care about spelling errors, but this one means a lot to me.
I gotta know, Dude.
Did she stop?
As I was constructing my post advising the mods, it occurred to me that was a bad idea, but it was already phrasing itself in my mind and insisted on coming out.
3 pints Carlsburg + 2 Irish coffees in a country where the average Irish coffee is about three times as strong as anything you’d get in the US.
1 2/3 bottles assorted cheap wine + 1 plate spaghetti
6 vodka screwdrivers + 1/2 joint + 1 sexual encounter with a total nutjob
4 pints Guinness + 1 shot Bailey’s + 1 bottle Mai-Bock + 2 unfiltered hand-rolled cigarettes
Oh, and on the non-alcoholic front:
Hitching a ride from DC to Chicago with a couple of total strangers in order to attend a three-day Marxist summer school.
Accepting an under-the-table job at the American equivalent of a cram school because it “seemed like a useful experience.”
Hmmm … on second thought, most of these were useful experiences, though not much fun at the time. No real regrets.
Not taking a semester off last year.
Not taking a semester off this year.
Taking honors O chem.
Trying to teach my boyfriend Spanish.
Bad idea.
Got…um…distracted too much.
We both gave up, and now my room is filled with Spanish books.
Yeah she stopped, but a little too abruptly. I went sliding off the hood, rolled across the road and into the ditch. I lost a little pride and a lot of skin that night.
Drinking nearly 40 oz of vodka within a 45 minute period. With lime concentrate. Upon further reflection, it wasn’t such a good idea.
Getting married because I was pregnant.
Going back to school with four children; a 2 year old, a 3 month old I was still nursing, and two boys in soccer. What the heck was I thinking?
Making that left hand turn last year. The only good point was that with my car totalled, I got to buy the mini-van I needed. Of course, I also have a pin in my ankle now.
Letting Feynn talk me into keeping the kitten. Who knew it was so ill-tempered?
Cool. Most of mine would have backed over me.
Letting that girl ply me with drinks at a bar during college, and going home with her afterwards.
Thinking that love and support would be enough to help someone with clinical depression. (Heh, I feel like Obi-Wan Kenobi. “I thought I could teach him as well as Yoda. I was wrong.”)
Getting involved in office politics.
And on and on and on…
I just missed my political science 210 final.
At a friends house doing flaming shots of 151, he was tilting his head back for his shot and something caused him to sneeze, thereby turning the liquor into a mist which turned into a fireball which ignited his face. We didn’t mean to laugh but it was oh-so-funny like you would not believe until we realized that Ed was hurt and we were all too drunk to drive him to the hospital.
We then decided to call his mom for help and she took him away, calling us a half-hour later saying he had 3rd degree burns and would be crispy for life. Luckily he shows almost no scarring so we can make fun of him rampantly today, but at the time it was a real buzzkill…