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- When Thaddeus, a wealthy, bigger-than-life lawyer, suddenly learns he is dying, he sells all his worldly possessions and embarks on a final quest to find a young hustler that he once tried to rescue.
- Mockumentary look at Playgirl Magazine centerfold and 1992 Man of the Year, Dirk Shafer, who kept it a secret from the magazine that he is gay. Most of the film is a fictionalized retelling of Dirk's decision to send a photograph to Playgirl, his selection as a centerfold and then Man of the Year, his many TV interviews, his friend Vivian Paxton posing as his beard, and the pressures from his live-in lover to come out of the closet. Interspersed with this chronological narrative are a black and white look at an evening Dirk spends with Angela Lucassey, a woman from Reno who wins Playgirl's national contest to have a date with Dirk, and an interview with a stripper who tracks Dirk down.
- After a night out at the club Babylon with Michael, Emmett and Ted; Brian picks up a cute guy named Justin for a night of fun.
- Lindsay and Melanie have a bris for their new baby Gus, which Brian decides to miss until Michael convinces him otherwise. Meanwhile Ted finally gets lucky with a guy, but ends up with devastating results.
- Michael fends off the romantic interest of a female coworker who doesn't know he's gay and instead dates a handsome chiropractor, while Brian is propositioned by a potentially lucrative client of his firm.