|Jenny and Nate|
|Nickname:||Nenny, Jate, NJ|
- “You're a really special girl, Jenny, and you deserve someone who's going to see that.”
- —Nate to Jenny[src]
Jenny and Nate date in Season 2 for a brief time. They are secretive at first because Jenny is worried Vanessa - 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. She sabotages Vanessa causing Nate to realise that Jenny will always be three years younger than him and nothing he ever does will change that, however Nate still cares deeply about Jenny. He chooses Serena over her though and this is one of the key reasons that Jenny sleeps with Chuck and gets banished in the first place.
In the novels, Jenny and Nate date only when Nate isn't with Blair. Jenny and Nate '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. 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. At the end of the series, Nate tries to confess his love for either Blair or Serena.
In Season 1 Jenny and Nate are purely platonic, he looks out for her when she becomes involved with the mean girls and thinks of her as a little sister.
Season 2EditSeason 2 opens with Nate kissing Jenny in on the streets of New York. Meanwhile, Jenny is uneasy about dating Nate because she fears that he doesn't reciprocate her feelings. She is also afraid of ruining her friendship with Vanessa, who had previously dated Nate. However, an infatuated Jenny ultimately decides to continue the relationship.
Unbenownst to Dan, who hates the idea of his friend dating his younger sister, Nate and Jenny continue their clandestine relationship. The two even manage to infuriate Vanessa by sharing a passionate kiss during Jenny's fashion show. Jenny, realizing that her worst fear has come true, runs after Vanessa and tries to smooth things over with her best friend.
Meanwhile, a distraught Nate sends Jenny an apologetic letter confirming his feelings for her and his frustration over how to continue their relationship. However, a jealous Vanessa is able to intercept the letter before it reaches Jenny, effectively keeping Jenny in the dark about Nate's feelings for her.
Because Jenny doesn't know about Nate's letter, she decides to gravely humiliate Vanessa. This plan ultimately backfires: Nate is disgusted by Jenny's viciousness and decides to pursue Vanessa instead.
Season 2 ends with a heartbroken Jenny watching from a distance as Nate and Vanessa rekindle their relationship and grab some coffee.
In Season 3 Nate is constantly looking out for Jenny, protective of her, and is constantly saving her from whatever trouble she gets herself into. Jenny and Nate dance together at the ball when Eric and Blair's sabotage fails. Jenny still likes Nate and spends lots of the series attempting to break Serena and Nate up so she can be with him instead. They spend the beginning of his birthday together, and they seem to be happy and playful together. Jenny's plan doesn't work and when she kisses Nate, he realises her plan from the start, he tells her that he wants to be with Serena.
Jenny is especially humiliated when Serena gets mad at her, she sleeps with Chuck and is the one who takes the photo of Serena and Dan in bed together. Once she sends this to Gossip Girl she knows it will break up Serena and Nate, but because of her being banished she still isn't with him.
Jenny: "Please, Nate, please don't go. I really need you here."
Jenny: "I'm a Humphrey; so syrup is a food group."
Nate: "How are you not five hundred pounds?"
Jenny: "What's wrong with me?"
Nate: "Nothing's wrong with you."
Jenny: "Why do you care so much?"
Nate: "You're a really special girl, Jenny, and you deserve someone who's going to see that."
Jenny: "Did I mention public embarrassment is part of the Humphrey birthday tradition?"
Nate: (Chuckles) "I think I'm actually glad to be humiliated."
Jenny: "Good. Now blow out your candle and make a wish, boy."
Nate: (Grunts playfully and blows out candle).
Jenny: (Laughs and claps) "Yay!"
"It's just whenever I'm alone I can't not think of the other night, you know? It's just, you're the only one who gets what I'm going through."
- Jenny to Nate.
Jenny: "Gee, thanks. As if it wasn't embarrassing enough when you fell asleep in the middle of my sentence."
Nate: "What, you mean monologue?"