Are you a Gossip Girl fan who believes Nate and Jenny should have been endgame? Well, we’ve rounded up 10 legitimate reasons why Nate ultimately rejected Jenny. It’s true that tons of fans loved the intensity and passion Nate and Jen had for each other, but there are also 10 big reasons why their relationship would have never worked.

Dan did not approve.

When Dan first spotted Nate and Jenny sharing a kiss, it pissed him off. In fact, it pissed him off so much that he kicked Nate out of the Humphrey loft at a time when Nate had no other place to go. Nate was temporarily living with the Humphreys in Brooklyn, but Dan wasn’t about to let that continue after finding out Nate had the hots for his little sister, Jenny. Dan and Nate also had a friendship between them, which means Nate sort of abandoned Bro Code to pursue his romantic connection with Jenny. One of the reasons Nate and Jenny didn’t work out was because Nate didn’t feel like he’d ever get approval or acceptance from Dan.

She dated a drug dealer knowing Nate’s father was an addict.

Nate never had the opportunity to talk to Jenny about the seriousness of her drug dealing stint, but the psychology of what she did might go a little deeper than what viewers saw on the surface. Nate dealt with the aftermath of his father, Howard, going to prison for fraud and embezzlement. Howard went down the rabbit hole of white collar crime because he had a drug addiction to fund. The fact that Howard was addicted to drugs pretty much ruined Nate‘s life. Howard financially destroyed everything for Nate and at one point, Howard even punched Nate in the face because he was blitzed out on cocaine. Jenny was complicit in drug dealing after knowing Nate’s father get locked up for an addiction, and that might have been the biggest turn off to Nate ever.

She sabotaged Vanessa with a see-through dress.

When Nate saw that Jenny was capable of being so evil and vindictive by sabotaging Vanessa‘s dress, he was totally turned off by her. Nate was usually the type of guy who preferred to do the right thing whenever he had the opportunity. For that reason, he never even sent in a Gossip Girl blast or spread a rumor about anyone in his friend group. As you can imagine, he was never the type of guy who was attracted to scheming and medaling. Jenny was giving it her all trying to fight for Nate when she sabotaged Vanessa, but she really shot herself in the foot by doing that because Nate was disgusted.

She tried to seduce Nate while he was dating Serena.

Nate got super turned off by Jenny once again when she tried to steal him from Serena. Nate waited his entire high school life for the opportunity to date Serena on a serious level. Serena finally gave him a chance after they graduated. They entered a committed relationship and Nate was ready to take it seriously! When Jenny started trying to sabotage the relationship by doing shady things to butcher his connection with Serena, he was able to call it out for what it was. The desperation Jenny was exhibiting by trying to seduce him from Serena did not garner his attention in a positive way. Ultimately, it actually thoroughly pissed him off. He ended up yelling at Jenny to “get out“ after uncovering her sabotage attempts.

Nate had to save her from the creepy photographer and roofie incident.

Nate was definitely a gentleman when he showed up to stop Jenny from having nude photographs taken of her, but the fact that he had to intervene in that way might have later become a bit of a turn off to him. The fact that Jenny willingly put herself in such a shady situation wasn’t cute at all. In fact, it possibly could have left Nate thinking about how immature she was, which would’ve been a huge reminder of her age. Since Jenny was a couple years younger than Nate, she already lacked the level of maturity and depth he was interested in. Then she went off making idiotic choices that reminded him of how young and dumb she really was. Later, Nate showed up again to rescue Jenny the night she was roofied. The only reason she was roofied is because she allowed Agnes to have direct access to her once again after Agnes already proved she could not be trusted. Nate having to show up and save the day for Jenny on multiple occasions made her look like more of a liability than a potential girlfriend.

He tattle-taled on her to Rufus for her own protection.

At one point, Nate teamed up with Serena behind Jenny’s back to prevent her from hooking up with Damien Dalgaard. Serena found out Jenny was considering swiping her V-card with Damien, so she told Nate to take Jenny to lunch as a distraction. Then they secretly called Rufus Humphrey to come pick Jenny up. Jenny felt beyond betrayed by Nate when he did that to her. And honestly, it was just another sign of how childish Nate saw Jenny to be. He didn’t think of her as his equal. He didn’t see her as an intelligent young woman who could make her own healthy decisions about her body and sexuality. If anything, his decision to call her father to come cockblock her was a sign that he thought of her as a little kid who needed to be shielded from the world.

She slept with his best friend, Chuck.

Nate never spoke on Jenny’s hookup session with Chuck, but let’s be real. This is likely another huge reason why it never would’ve worked out between Nate and Jenny. The only guy on Gossip Girl whoever treated Jenny with real love and respect was Nate. If anything, she should have saved her virginity for Nate or someone who treated her just as well as him. Instead, she turned to Chuck in a moment of loneliness, even though it was an extremely self-destructive decision to make. Despite the fact that Nate never made a comment about Jenny and Chuck’s intimate evening, that might’ve been one of the reasons Nate realized he could never take her seriously.

She was turning into Blair, and he didn’t want to date someone like Blair.

Nate and Blair‘s relationship didn’t work out for a handful of reasons. Ultimately, they broke up because they realized their relationship wasn’t meant to last beyond high school. But still, there were things Blair did along the way that turned Nate off! The fact that Blair was such a manipulative schemer was definitely not his vibe. Over time, Jenny was morphing into Blair 2.0. Nate never outright complained about the ways Jenny was changing and becoming more similar to Blair, but it’s safe to assume her personality switch-up wasn’t something he was vibing with. Jenny went from a sweet and innocent girl who cared about fashion to someone who bullied her close friends, sent ruthless Gossip Girl blasts, and betrayed others for her own personal gain. That’s just not the type of girlfriend someone like Nate would care to have.

Long-distance dating would have never worked between Hudson and Manhattan.

After Jenny hooked up with Chuck, Blair banished her from the island of Manhattan. Blair was obviously pissed because she was betrayed by Chuck, who was supposed to be the love of her life and Jenny who she selected as her Queen Bee successor at Constance. Jenny was forced to relocate to Hudson. If you really think about it, a long-distance relationship never would have made any sense for Jenny and Nate since she was stuck in Hudson while he stayed in Manhattan. The frustrations that come with long-distance dating alone likely would have been enough to butcher Jenny and Nate’s relationship if they tried to make things work.

He always seemed to have stronger feelings for other girls.

The last biggest reason why we believe Nate rejected Jenny is because his attraction to other girls always seemed to trump whatever attraction he had to Jenny. We saw it happen in the most aggressive way when he needed to choose between Jenny and Vanessa. He chose Vanessa. Then, we saw it happen when he had to choose between Jenny and Serena. He chose Serena. Whenever Jenny was going head to head against another girl in pursuit of Nate’s heart, she was never the one Nate would choose. Nate had a long list of girlfriends on Gossip Girl including Bree Buckley, Sage Spence, and Raina Thorpe. Just name a few. We might bet a few bucks that if Nate had to choose between Jenny and any of his other girlfriends, Jenny would lose against them as well.

Do you think any of these are valid reasons for why Nate ultimately rejected Jenny on Gossip Girl? They certainly didn’t end up together by the finale episode of the show. Leave your thoughts in the comment section below.