Question: who does blair lose her virginity to in the books

title: Jenny Humphrey
text: At Rufus 's suggestion , Eleanor reemploys Jenny to help out with her upcoming fashion show . Jenny is happy to be back , but is shocked to learn that one of the models she 'll be working with is Agnes , who , after the show finishes , takes revenge on Jenny by drugging her and leaving her in a bar to be taken advantage of . Nate rescues Jenny before anything happens to her . Because of this , Jenny 's feelings for Nate reawaken and she aspires to win him over . She tries to kiss him but he resists her advances because he sees her only as a friend and because he is dating Serena . Jenny attempts to sabotage Serena and Nate 's relationship by lying to Serena and implying to Nate that she is having an affair with Carter Baizen . Jenny 's attempts fail , and her relationship with both is left tenuous after Nate kicks her out of his apartment .