Did you adore or despise Jenny Humphrey on Gossip Girl?

She was a significant character in the first three seasons of the show, but her presence was dialed back from Season Four through the finale.

Still, Jenny certainly left a lasting impact on viewers since she was always so polarizing.

Here’s a breakdown of the 10 best Jenny Humphrey-centered episodes on Gossip Girl you might want to rewatch if you are a true Jenny fan.

Seventeen Candles.

In the episode titled Seventeen Candles, Jenny shared her first real heartfelt conversation with Nate Archibald. That episode laid the foundation for what was to come in the future between Jenny and Nate. Jenny’s feelings for Nate were always a big deal on the show, even if they didn’t get to have their happily ever after moment together in the end. Jenny and Nate connected on the steps outside of Blair‘s 17th birthday party. Nate knew he should have gone upstairs to celebrate with Blair, but he was too distracted with all the drama going on with his parents at the time. Technically, it all worked out because Blair got to stay upstairs celebrating with Chuck Bass, who ended up being her perfect match. Nate took the time to communicate with Jenny about his emotional state of mind, and Jenny was there to nurture him and comfort him. Nate‘s perception of Jenny in this episode was absolutely gold!

Dare Devil.

In an episode called Dare Devil, Jenny prove that she was an absolute badass after attending Blair‘s annual sleepover. Blair invited her to the sleepover with the worst possible intentions ever. Blair pushed Jenny to drink alcohol underage and insisted all the girls agree to play a game of Truth or Dare. It wasn’t just any typical game of Truth or Dare, though. Innocent Little J brought up a time she played Truth or Dare and had to eat an entire bag of marshmallows! But that wasn’t the type of Truth or Dare game Blair wanted to play. In Blair‘s world, Truth or Dare included girl on girl kissing, and even a little bit of stealing. Blair set Jenny up to get arrested after daring her to steal a jacket from Eleanor Waldorf‘s store. Fortunately, Jenny was able to talk her way out of the situation when cops arrived on the scene. The reason Jenny was a true badass in this episode is that she showed up at Blair penthouse after all was said and done, and she boldly kept the jacket she stole from Eleanor‘s store!

The Dark Night.

Jenny’s talents as a fashion designer were placed on full display in an episode called The Dark Night. That’s because Eleanor Waldorf fired her in the heat of the moment before rehiring her not long after. You can say a lot of negative things about Jenny on Gossip Girl, sure, but one thing you can’t deny is that she knew exactly what she was doing with a sewing machine. Eleanor initially fired Jenny because she overheard Jenny crossing the line by critiquing some of Eleanor’s designs. After a power outage caused New York City to shut down, Eleanor spent more time hanging out with Jenny and realized she did indeed want to keep Jenny’s internship going strong. Jenny might’ve criticized Eleanor‘s skill set as a designer, but Jenny’s personal skill set as a designer is what saved her in this episode.

New Haven Can Wait.

In an episode called New Haven Can Wait, Jenny finally got her way with her father, Rufus Humphrey. Jenny was desperate for a chance to start the homeschooling process so she could spend more time focused on her career as a fashion designer. At first, Rufus was completely resistant to the idea. He wanted Jenny to go to school like other teenage girls and prioritize her education above all else. Jenny got help from Vanessa Abrams in convincing Rufus that homeschooling would be a viable option since Vanessa spent years of her life being homeschooled as well. Ultimately, Rufus agreed that Jenny could finish high school in a homeschooling capacity, and that was a massive win for Little J.

There Might Be Blood.

In an episode called There Might Be Blood, Jenny went balls to the wall with her guerrilla fashion show. It was one of the edgiest and most shocking things Jenny could have done in Season Two of the show. Jenny was confident that she’d be able to successfully make it as a fashion designer, and she didn’t want anyone or anything to hold her back. Working for Eleanor Waldorf was great for a while, but ultimately, Jenny’s dream was to make it on her own with her own name on every label. She crashed Bart and Lily’s event to host her guerrilla fashion show with the help of Agnes Andrews and other hot young models to garner attention from wealthy people on the Upper East Side. Although Jenny’s plan was super unorthodox, it worked in her favor because she got a lot of positive attention and traction from it. When cops arrived on the scene, her father was so offended that he encouraged police to take her in. Lily intervened and told the cops that she was totally fine with the guerrilla fashion show, seemingly protecting Jenny from getting arrested. Jenny might’ve lost more trust from her dad in this episode, but her fashion career was certainly on the up and up.

The Goodbye Gossip Girl.

In an episode called The Goodbye Gossip Girl, Blair chose Jenny to be her successor as Queen Bee of Constance. Blair knew it was time for her to graduate and move on to a college lifestyle. However, Blair still wanted to make sure she was leaving Constance in good hands by choosing a Queen Bee who would run things just as well as she did when she was a student. Blair made Jenny compete for a chance to be selected, and Jenny rose to the occasion with flying colors. The rule for winning the game is that whoever brought Blair the juiciest piece of gossip would take the crown. Jenny accomplished that with ease. Instead of putting on an actual tiara, Jenny wore a crystal covered headband in honor of Blair‘s fashion sense when it was time for her to fully take over. It was a winning moment for Jenny, who spent the previous year clawing her way into relevancy by trying to fit in with wealthy girls on the Upper East Side, even though she was from Brooklyn.

Pret-a-Poor-J.

In the episode called Pret-a-Poor-J, Jenny had the opportunity to connect with Nate Archibald on an emotional and physical level. That’s because he intervened and saved her from a nearly nude photo shoot that could have possibly ruined her life. The last thing Jenny needed was for nude photos to be circulating of her when she was still underage. It would’ve been totally illegal and it would’ve ruined her reputation in New York City. Nate busted in and stopped that from happening, and when they were talking to each other outside, they ended up sharing a passionate kiss. Granted, Nate was frustrated with Jenny for putting herself in such a sketchy scene, but it was still the moment when he felt the most comfortable revealing his romantic feelings for her. Since Jenny had been crushing on Nate for so long, that moment was genuinely a dream come true for her.

The Sixteen Year Old Virgin.

Although a lot of negative drama went down in an episode called The Sixteen Year Old Virgin, it was still one of Jenny’s best episodes on the show since she showed tons of self-respect and self-preservation by NOT having sex with Damien Dalgaard. She was dating Damien and their relationship was incredibly toxic. He acted bored and uninterested in her at first, then he enlisted her help to sell drugs to wealthy customers on the Upper East Side. Then he started aggressively pushing her to have sex before she was ready. The reason this episode is one of Jenny’s best is because she walked out on Damien after he tried to diminish the importance of her virginity. After she confessed that she was a virgin, he brushed her off and made it sound like it wasn’t a big deal. He still expected her to sleep with him, no matter what. After she told him she simply wasn’t ready to do it yet, he told her she was a kid! Instead of caving to the pressure, Jenny walked out on him without giving him the satisfaction into his manipulation.

Easy J.

In an episode called Easy J, Jenny resurfaced in Season 4 for an important meeting with Tim Gunn. Tim, who’s known for being one of the most iconic individuals in the fashion world, was excited to sit down with her after Chuck Bass arranged for them to meet. This was a powerful episode for Jenny because she already relocated to Hudson, but she ventured back to New York City specifically to sit down with Tim. Her interview with Tim was disturbingly sabotaged at first, but Jenny didn’t allow that to ruin everything. She tracked him down later on at a party to explain what happened, and he agreed to give her another chance. This was a great episode for Jenny since it proved she was willing to put herself in the line of fire regarding Blair‘s rage in order to pursue her dream of becoming a successful fashion designer in the Big Apple.

New York, I Love You XOXO.

The finale of Gossip Girl was pretty chaotic since it was stuffed with so many different things as the show writers tried to bring closure to viewers. One of the reasons this episode was such so brilliant for Jenny specifically is that she showed up to support her big brother on his wedding day to Serena. At the very beginning of the show, Jenny encouraged Dan to pursue a relationship with Serena by helping build his confidence and giving him advice to fight for a chance since Serena was always his dream girl. It was a full circle moment to see Jenny present on his wedding day with Serena. The finale also revealed that Jenny went into business with Blair Waldorf for a fashion company called J For Waldorf. That revelation was amazing because Jenny and Blair spent so much time feuding with each other. Knowing that they ended up on good terms with the ability to work together spoke volumes about their growth as friends.

They Shoot Humphreys, Don’t They?

Jenny’s best episode ever beyond all 10 of the episodes we just listed off definitely has to be the episode when she arrived at her Cotillion. In the episode called They Shoot Humphreys, Don’t They? from season three, Jenny showed up at Cotillion wearing a stunning black gown. Eric was trying to sabotage her from having a successful night, but her evening still turned out wonderfully because Nate showed up to be her date. Since Jenny’s feelings for Nate were always lingering, him showing up as her Cotillion date was a total win. On top of that, Jenny looked absolutely divine since her dress, hair, and makeup all came together flawlessly. She was like a Gothic Barbie doll.

Which of these Jenny-centered episodes was your favorite while watching Gossip Girl? Let us know your thoughts in the comment section below.