One True Pairing: Jenny and Nate’s best moments in Gossip Girl

Welcome back to our usual appointment with One True Pairing, the column dedicated to the most beautiful couples of the TV series: this time we analyze the relationship of Jenny and Nate from Gossip Girl

Although the most loved love affair in Gossip Girl is that of Chuck and Blair, that of Jenny e Nate it is undoubtedly the most unexpected. With Nate still secretly in love with Serena, we never expected him and Jenny to get close romantically.

Although there was no happy ending to their story, the two boys spent unforgettable moments together.

The best moments of Jenny and Nate in Gossip Girl

1. The masked ball

During a masquerade ball organized by Blair, Nate mistakes Jenny for Serena, and confesses that he has never forgotten her. Nate immediately realizes the misunderstanding, and so asks Jenny not to tell Blair about the evening by offering her a box of chocolates. It is the beginning of their journey.

2. A friend

On the evening of Blair’s seventeenth birthday, both Jenny and Nate are hesitant about whether or not to go celebrate her. That same evening, when they bump into each other, they start chatting and getting to know each other better. Nate reveals her doubts about her family, and Jenny is there to listen to him and give him advice without judging him.

3. Cotta

During the second season, Nate loses everything he has and Dan invites him to stay with him until his situation improves. Living together with the Humphreys, Nate begins to see Jenny in a new light, no longer as a friend, but as a potential love interest. He is admired by her grit, tenacity and dedication to work as a stylist.

4. “Why do you care so much?”

Jenny begins her internship at Eleanor Waldorf’s atelier. Here he meets the model Agnes, who involves her in a private party with a photographer who takes photos of them in their underwear. Nate takes her away and points out that the man was taking advantage of her. When Jenny asks him why he cares so much about her, Nate is left speechless and kisses her.

5. The parade

Together with Agnes, Jenny plans to improvise a rebel fashion show in the middle of an evening organized by a philanthropic company. Little J arranges everything in great secrecy, except for Nate, to whom she confesses her plan and asks for help. Nate supports her and gives her all the help possible so that everything runs smoothly during the show.

6. Jenny’s social debut

When Jenny’s corporate debut is sabotaged, she finds herself without a chaperone. Debuting on her own would be a real humiliation for the new queen bee of the Upper East Side, and it is precisely in her time of need that Nate rushes to her aid by becoming her date himself and dancing with her throughout the evening.

7. Nate cares about Jenny

Little J starts dating Damien, an older boy who turns out to be a drug dealer. The girl’s friends and family try to dissuade her from being with him, but Jenny’s rebellious spirit pushes her to get even closer to him. When Nate finds out that Jenny is thinking about losing her virginity to Damien, he goes to great lengths to get her away from the dangerous guy, even if it means getting her to hate her and betray her trust.

8. Nate saves Jenny

About a year after their fight, Jenny meets Agnes again. The model is still angry with J. and enacts a wicked revenge: drugs and takes her to a pub where a slimy man tries to take advantage of her. Luckily Nate notices what is happening and immediately catches up with her, saving her once again.

9. Backfire

After what happened with Agnes, Jenny begins to wonder how she got to that point. Nate stays by her side making her understand that nothing of what happened to her is her fault, embracing and heartening her. Nate’s comforting words trigger something unexpected in Jenny, and she finds herself still in love with him.

10. Awakening

In the last handful of episodes of the third season, Jenny finds herself alone and feels abandoned by all her friends. The only one who remains next to her is Nate, who lets her spend the night with him making her vent and heartens her by telling her that for her, he will always be there.


While they’re only really together for a few episodes, Jenny and Nate’s fates meet from the start and intertwine again and again over the course of the series. For Nate to have someone like Jenny to confide in, someone from outside the Upper East Side scion circle is a relief. For Jenny, on the other hand, Nate becomes a lifeline on numerous occasions.

Both bring out the best in each other, supporting each other and always remaining united, both as friends and as lovers.