There is literally no other girl or boy on the show that Nate or Jenny have a nicer/more positive relationship with (except for Eric with Jenny but obviously that’s not going anywhere romantic). I feel like, if they were to marry anyone in the show, it would be each other because their relationship is so much more wholesome than anyone else’s.

Nate and Jenny date in Season 2 for a brief time. They are secretive at first because Jenny is worried Vanessa Abrams, who is like a sister to her, will find out about their relationship. However, when they kiss and Vanessa sees, Jenny runs away from Nate effectively ending the relationship.

After breaking up with his girlfriend, Blair, Nate meets Jenny in Central Park and they begin a brief romantic relationship. In the short time they date, Nate buys her thong underwear and the two are accidentally filmed fooling around by Vanessa in a video that goes viral.

In the Gossip Girl novel series, Nate and Jenny date only when Nate isn't with Blair Waldorf. Nate and Jenny "fool around" in Sheep's Meadow while Vanessa films them. After this fiasco, the two don't reunite until the final book, in which Nate goes to a party with Jenny rather than Blair or Serena.