In the Gossip Girl novel series, Nate and Jenny date only when Nate isn't with Blair Waldorf. ... In I Will Always Love You, Jenny eventually reunites with and loses her virginity to Nate, and they date seriously for a while until Jenny pursues Blair's younger brother, Tyler Waldorf.

Do Nate and Jenny ever sleep together?

Meanwhile, Jenny goes to Chuck's hotel to hang out with Nate but instead finds a sad Chuck drowning his sorrows by getting drunk and Jenny joins him as she is also depressed and has hit rock bottom. Eventually, the two have sex and Jenny finally loses her virginity.

Who did Nate end up with?

She too believes that he and Blair are more than just friends, and confronts Nate, who is upset that Vanessa doesn't trust him and breaks up with her. Nate then renews his relationship with Blair and they become a couple again (Remains of the J).