This guy was painfully shy around me, never spoke; he could only write letters and send mix tapes full of R.E.M. to express himself. He was intense, artistic, mysterious, and pretty cute—so I tried to make something work. One night, we had a drink and went for a walk. He started to talk, open up, then stumble around and fall down. Then declared that he loved me. He was so drunk, I had to carry him home and put him to bed. I guess the only way we could converse was if he was smashed.

—Sasha

Aftermath: We never spoke of that night. In fact, we never spoke again. Technically, we weren’t even dating, as that supposes a two way street of shared experiences—and there was nothing but awkward silence.

On our third date, I met a guy at his house. He was showing me pictures in a photo album. When he came to a picture of himself, he said “There she is, in all her finest!”

—Brian

Aftermath: We did not have a fourth date.

I realized it was over when I wanted to spend more time with my mom and her 25-year-old boyfriend than with my boyfriend.

—poemgirl

Aftermath: I used my mom as an excuse to dump him — “she didn’t approve” of my dating him.

When I was 19, I dated this country boy while I was home from college for the summer. I knew it wouldn’t work when he showed up for a date one night in a Hooters T-shirt, cut-off shorts and high-top shoes. Then we went to a gravel pit and made out in the back of his pickup.

—Summer

Aftermath: It was fun while it lasted (about a week), but we would never have made it past that “What does it all mean?” conversation.

When we were in bed spooning one night, and my arm fell asleep underneath her. As I went to slide my arm out, she turned around and said, “What’s wrong with you? Don’t you love me?” She rolled over and bawled for the next hour, inconsolable.

—Michael

Aftermath: Two months later, we were through. After my arm fell asleep, there was a constant boo-hoo over everything. I couldn’t take it.