Dear Tell All: I like this woman who is admittedly out of my league. Jessica -- not her real name -- is gorgeous, witty and talented. I, sadly, am not. But we are friends, and I've done a pretty good job of keeping my adoration to myself, thinking I'd never have a shot with her.
We have a mutual friend I'll call Carrie. Carrie and I had a flirtation last summer that never went anywhere. It didn't seem like a big deal -- not to me, anyway, and I thought not to Carrie, either.
But recently Carrie and I were talking about Jessica, and she picked up on the fact that I have a crush on her. She jumped on this piece of news and insisted that I'd have a chance with Jessica if I asked her out.
That floored me, and I asked Carrie dozens of probing questions over the next week to determine if it was really true. According to her, it was. I assumed she'd let Jessica know about our conversation, the way girlfriends do. If Jessica went "ewww," Carrie would let me know that I should back off.
She never told me that, so I figured I had the green light. I got up the nerve to ask Jessica out -- and guess what? She hemmed and hawed, obviously taken aback. She sheepishly said yes but ended up sending me a Facebook message the next day to back out.
So now I'm left trying to figure out what happened. Did Carrie really think I had a chance with Jessica? Or did she deliberately sabotage me as revenge for our failed flirtation last summer?
I admit that I don't understand women in the slightest.
Dear Dumped: I vote sabotage. But then again, I always choose the most paranoid option -- or at least I have ever since Lyndon Johnson colluded with the Cubans and the Mafia to assassinate John F. Kennedy.
Readers, help me out. Was it an innocent mistake, or was Dumped set up to fail?
Do you have a question about life or love in Madison? Write Tell All, 101 King St., Madison, WI 53703. Or email firstname.lastname@example.org.