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Tuesday, September 16, 2014 |  Madison, WI: 43.0° F  Fair
The Paper
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Tell All: Don't have sex with a friend
I did and still regret it

Dear Tell All: I have the opposite problem of the Biggest Loser, your letter writer who never got around to telling his lifelong female friend that he loved her in a romantic way ("The One Who Got Away," 2/14/2013). If only he'd had the nerve to confess his real feelings to her, he said, he and his beloved could have found eternal bliss.

Guess what? That probably wouldn't have happened. I was in a similar situation with a college friend. We met freshman year and bonded immediately. It was easy to have intimate conversations with her, where both of us talked freely about our deepest feelings.

I held back only one of my deepest feelings: a yearning to be involved with her. This secret wasn't crippling or anything. I never expected that a romantic relationship was possible, so it was easy to continue as just friends.

Then came the last day of college. We stayed up late with mutual friends, had a lot to drink, and walked back to her apartment. We were both feeling emotional about school ending. I'm not exactly sure how it happened, but we started kissing, and before long our clothes came off. It should have been the greatest moment of my life, but I made the mistake of saying "I love you" more than once. I could feel her pulling away, and deep embarrassment set in on both sides.

The next day, I was horrified by how distant she'd become. It's as if I weren't her close friend anymore, but a one-night stand that she wanted to distance herself from.

We've kept in touch, but only sporadically. I can't help thinking that our friendship soured that night. Biggest Loser, you should count yourself lucky that you kept the relationship with your beloved on a platonic level.

Biggest Idiot

Dear Idiot: I'm confused about the lesson to draw from these letters. Biggest Loser says you're damned if you don't confess your true feelings to a friend; Biggest Idiot says you're damned if you do. Readers, is there no way for a guy in this situation to live happily ever after?

Do you have a question about life or love in Madison? Write Tell All, 101 King St., Madison, WI 53703. Or email

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