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After briefly serving as frontman for the band The Raves, he hooks up with one of the instrumentalist's wives and later experiments with being gay.He eventually attends Evergreen State College but realizes he truly loves Vanessa.Rusty also manages a novelist named Mystery Craze, whom Dan is attracted to.At a poetry reading, the two hook up, and Vanessa witnesses.Meanwhile, the two become friends with celebrity student Olivia Burke.Dan begins dating her and all is fine until the three engage in a threesome (They Shoot Humphreys, Don't They? Afterwards, Olivia is hurt, due to her seeing Dan and Vanessa ice her out during their threesome.
Despite this, they rekindle their friendship and hang out again.In The Handmaiden's Tale, Vanessa appears at the Humphrey loft in Brooklyn to announce that her parents have let her move back to New York to live with her sister, Ruby.However, things are awkward between Vanessa and Dan, as they left things roughly before she moved, due to Dan telling Vanessa that he loved her as more than a friend.Afterwards, she moves to Spain and passes the royalty check on to Dan.After being friends for years, Dan realizes he has feelings for Vanessa and the two enter into a relationship.
When they were 16, Dan told Vanessa he loved her as more than a friend but she rejected him, as her family was moving to Vermont.