Season 1, Episode 5 Kyle Dates Up
First Aired: April 14, 2006
Kyle is challenged to date an intellectual woman, so Molly sets him up with a classmate. When the woman doesn't show, he and Molly hit it off, causing Tim to end their friendship.
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- Premiered: March 17, 2006
- Rating: None
- Premise: Three single men look for love in Chicago with help from a female life coach. The trio have been friends since childhood and all have different problems with women. Tim's girlfriends always dump him; Doug can't get over his ex-wife; and Kyle is a Casanova-… (more)