he has been dating blair since middle school. however, nate is shown to have deep, unresolved feelings for serena. they have sex during the summer at a wedding. he reveals this to blair in the first novel after serena returns, and right before they were supposed to lose their virginity to each other, which causes their first breakup. he gets together with freshman jenny humphrey, but later dumps her for blair for being too clingy. he and blair have an on-again-off-again relationship throughout most of the novels.