After being expelled from Constance, Jenny is able to convince her father, Rufus, to let her attend Waverly Academy, a boarding school located in upstate New York.

In the Gossip Girl prequel It Had to Be You, Jenny is noted for having a rather flat chest until she begins taking breast enlargement supplements, which are the cause of her DD-cup size.

Jenny is the protagonist of the book series The It Girl, which shows her new life after she gets expelled from Constance Billard and starts at Waverly Academy in upstate New York.

Jenny then meets her two new exceptionally beautiful and popular roommates: lithe and blonde Southern girl Callie Vernon, and red-headed, green-eyed, sophisticated New Jerseyan Brett Messerschmidt.

Lacking self-confidence because she is not as rich as the other girls, she sells her sewing machine and barters an expensive dress she stole from one of her friends.

He convinces her to say that she lost her virginity to him in order to dispel the rumors that he is gay, promising that as long as she pretends it's true, he'll give her privileges that the Upper East Side can offer.

He forgives her and invites her to the White Party in the Hamptons, where he introduces her to Tinsley Mortimer and she proves her worth to one of Eleanor's supervisors.

In an effort to ruin Serena, Blair switches the final dress with one that Jenny made, drawing Eleanor's ire.

At work, Jenny befriends Agnes Andrews (Willa Holland), a model who convinces her to start her own fashion line.

Jenny also begins a short relationship with Nate when they share a passionate kiss after he rescues her from being taken advantage of by an older photographer.

Agnes's fiery temper and their growing disagreements over the clothing line make it hard for them to close a business deal.

During the season finale and Serena's hunt for Gossip Girl, Jenny decides to compete to be the next Queen Bee after Blair leaves.

With her new position and wealth, Jenny's social-climbing persona resurfaces and she begins to erase her former Brooklyn self, throwing away her homemade clothes and sewing machine.

The plan backfires, and Jenny instead secures Nate to escort her, winning her the respect of the Queens at every prep school on the Upper East Side.

Liking his wild lifestyle, Jenny strikes up a relationship with him and helps him supply drugs to his customers while sharing in some of the profit, even stealing some of Lily's “headache pills”.

At a gala event where Serena's recently returned father William Van Der Woodsen is making a speech, a former client of Damien's approaches Jenny, angrily telling her the drugs she sold her (Lily's cancer medication) gave her a yeast infection.

During her punishment, Jenny researches Lily's medicine and tells Chuck there is something very wrong with the medication Serena's father is prescribing her.

It is discovered that William has lied to Lily about her condition and been giving her drugs that make her sick in a plot to win her back from Rufus.

Seeing an opportunity to break up Rufus and Lily and return her family to the way it was before, Jenny attempts to sabotage Blair, Chuck, and Nate's plan to unveil William's deception.

Jenny ultimately realises the damage of her return and decides to leave for good, telling Blair and Chuck that their vindictive games against each other will soon destroy them both.

In the premiere episode of season 5, "Yes, Then Zero", Rufus reveals that Jenny moved to London to attend Central Saint Martins.

In the final episode of the series, it is revealed that Jenny knew that her brother, Dan Humphrey, was the mysterious blogger behind Gossip Girl.

She returns to the Upper East Side, appearing in the five-year time jump for her brother's wedding to Serena van der Woodsen.

Rumors had circulated during Gossip Girl's first few seasons that Jenny would be given her own spin-off, in line with the character leaving for boarding school just like the novels.

Despite the illegality of it all, it was nice to see Jenny put her wit and wiles to use..."[2] Following the dramatic events during the third season finale, Michael Ausiello praised both Leighton Meester and Taylor Momsen's performance.

[6] When asked during a Vanity Fair interview if "real" girls could afford the looks from the show, costume designers Eric Daman and Meredith Markworth-Pollack commented on Jenny's style and stated "Of course!