Jake (the almost first kiss)

My freshman year of college, I went out a few times with this guy from Idaho. He was nice, cute, good at basketball... but not nearly as smooth as he thought he was.

One evening in particular, he seemed nervous. He drove me around town as if looking for something. Finally we pulled over next to what looks like a park bench...except that it was sitting in the middle of the sidewalk next to a semi-busy street. (So not romantic.) I could tell he was trying to make a move, but each time a car passed we were back to square one. After a few moments of quiet he said, "You know this park bench means a lot to me. It's where I had my first kiss." (Oh no.)

As his puckered mouth came at my face the only thing going through my brain was, "Whatever you do, Ami, don't laugh!" No such luck. The combination of the unromantic situation and the terrible line was more than I could handle. Just before he arrived, I pulled my head back in uncontrollable, evil, you've-got-to-be-kidding-me laughter.

He immediately stood up, walked to the car, and drove me home in silence. We didn't go out again.

Moe (my first date)

I thought my first date would be a good place to kick this off.

My very first date was about 6 months after my 16th birthday. One of my friends set me up with her quirky little brother so we could double with her and another guy she'd been wanting to go out with. The day of the "big date," her brother informed me that he wasn't interested in going on the date, but would do it for his sister... if he had to. Needless to say the date felt a bit awkward after that.

I think this was a serious omen as to where my dating life was headed. Had I only known...