Jenny and Nate had every chance to be the perfect couple on Gossip Girl, but Jenny couldn’t help herself from continually turning Nate OFF.

Jenny was always doing immature and stupid things that reminded Nate why they could never be together.

Ultimately, Jenny left the show early, and Nate ended the show single. If Jenny hadn’t turned Nate off in all these major ways, there’s a chance they could have been endgame.

Here’s a roundup of 10 times Jenny left Nate feeling totally repulsed.

The first time Nate had to warn Jenny about her blossoming friendship with Blair and the minions.

In an episode called The Blair Bitch Project, Nate pulled Jenny aside after noticing a change in her attitude. He warned her to be careful not to fall out of line with her friend group, but Jenny didn’t react well to that. She instantly got defensive when she said she wouldn’t fall out of line in any circumstances. Nate instinctively saw what was coming when he analyzed Jenny’s desperation to hang out with Blair and the minions. He didn’t want to see Jenny turn from an innocent and sweet girl into a coldhearted bully like Blair, but there was nothing he could do to stop it from happening aside from giving her his two cents.

When Jenny frantically called Nate, asking to borrow $8,000.

Another time Nate was thrown for a loop with Jenny was when she called him up, asking for such a whopping amount of cash. Jenny got herself into trouble when she stole from Hazel’s mother’s closet and tried to get quick money for it from a pawnshop. When she later realized how much the dress was valued at, she definitely didn’t have anywhere near $8,000 to get the dress back. She called Nate in a panic asking him to loan her the cash. Instead of shelling over the money, Nate immediately called Dan Humphrey to rat Jenny out. In that moment, Nate realized how capable Jenny was of making expensively stupid decisions.

When Nate busted in to save Jenny from a nearly nude photoshoot.

Nate was judging Jenny HARD after rescuing her from her nearly nude photoshoot drama with Agnes Andrews and a pervy photographer named Max. Jenny and Agnes were in the middle of stripping out of their clothing while Max was snapping tons of photos of them. If Agnes and Jenny had removed any more clothing, they would have become the subjects of some very illegal contents since they were both underage at the time. Nate tracked Jenny down, banged on the door, and escorted her out of there for her own good. When they got outside, Nate started scolding her because he was so annoyed that she would put herself in such a messed up situation. Still, he ended up kissing her that night because he realized he felt protective of her because he was crushing on her. However, Nate was still bewildered by Jenny’s decision strip out of her clothing in such a creepy environment.

When Jenny set Vanessa up to wear a see-through dress.

Nate made it abundantly clear that he was turned off by Jenny after finding out she was the one who sabotaged Vanessa at the Snowflake Ball. Jenny convinced Vanessa to wear a sheer dress that didn’t have any lining sewn in. Nate thought Jenny‘s actions were cruel and immature, and it actually ended up giving him more of a reason to cling to Vanessa, even though Jenny was competing against Vanessa for his attention. When Nate confronted Jenny at the Snowflake Ball, he asked, “Did you do that to Vanessa?” Jenny replied, “Yeah, but you don’t understand!” Nate cut her off to say, “Why, because she went behind your back? So what? For that she deserved to be publicly humiliated? She’s your friend!” Then, Nate handed Jenny an old letter he wrote to her where he expressed his feelings. In that same breath, he also let her know the letter was no longer relevant. That was a harsh moment of truth for Jenny.

When Nate agreed to take Jenny out to lunch to “babysit” her.

When Jenny was dating,Damien Dalgaard, Serena grew increasingly worried that Jenny would make the wrong decision with Damien in the bedroom. Serena didn’t want Jenny to swipe her V-card with Damien and find herself regretting it later. Serena went out of her way to protect Jenny from Damien to make sure nothing inappropriate happened between them before Jenny was truly ready. Serena enlisted Nate’s help to distract Jenny by taking her out to lunch so Jenny wouldn’t have enough privacy or free time to make the wrong choice. In a sense, Nate seemingly agreed to “babysit” her, even though she was his peer and at one point, she was even one of his own romantic interests. Nate agreeing to babysit Jenny was an indication that he didn’t think of her as an intelligent young woman who was capable of making coherent decisions on her own regarding her body and sexuality.

When Jenny boldly dated a drug dealer, knowing Nate’s dad was a struggling addict.

Nate was pissed at Jenny for dating Damien, and he berated her for getting into drug sales. We have no doubt in our mind that her choices had a negative impact on his perception of her. As a reminder, Nate struggled with the repercussions of his father‘s actions after his father was arrested and imprisoned for embezzlement and fraud. His father only got caught for white collar crime because he was also struggling with a drug addiction. Why would Nate maintain any sense of attraction for a girl who was willing to dated drug dealer and sell drugs herself? What makes matters even worse was that Jenny became a drug dealer for the most immature and selfish reason ever! She wanted to impress her minions by purchasing designer bags for them so she could maintain her status as Queen Bee. What a turn off!

When Jenny allowed Damien to punch Nate in the face.

In what world was it okay for Damien to punch Nate in the face? In an episode called the 16-Year-Old Virgin, Nate followed Jenny to a museum to give her more advice, warning her against making the wrong sexual decisions with Damien. He told her, “You’re a really special girl Jenny. You deserve a guy who’s going to see that. You know, one who’s going to be there in the morning.” Jenny brushed him off with the highest levels of dismissiveness. But the scene escalated when Damien strolled in to escort Jenny away. Nate boldly stepped in front of them to block Jenny from leaving, but Damien took matters and into his own hands by swinging at Nate with pure aggression. He knocked Nate down with a punch, and Nate accidentally also knocked down a cater waiter behind him. It was chaos!

When Jenny kissed Nate without his consent during a game of Assassin.

Jenny had no business planting a kiss on Nate’s lips while they’re playing a game of Assassin on his birthday. Keep in mind, he was in a full-fledged relationship with Serena at that time. Not only that, but Nate was actually really happy to be dating Serena! He’d been pining over Serena for years, so he was grateful to finally have an opportunity with her. But Jenny selfishly still kissed him while they were playing Assassin because she was desperate to steal him away from Serena so she could date him for herself. Jenny spent years crushing on Nate, and as time progress, she only got more and more aggressive and more and more bold with her approach. Nate‘s face after Jenny kissed him during Assassin spoke volumes, though. He was not enticed. Rather, he was completely turned off.

When Nate yelled at Jenny to “Get out!”

One of the most obvious times Nate was turned off by Jenny was when he fully yelled at her to get away from him after noticing multiple instances of Jenny trying to sabotage his relationship with Serena. Jenny knew Nate was feeling jealous about Serena‘s closeness with Carter Baizen, and she used that to her advantage. Serena was only hanging out with Carter because Carter was helping her track down her father, and Nate was feeling slightly insecure about it. Jenny knew Serena was loyal to Nate, but she tried to convince Nate that Serena was truly a cheater. When Nate had Serena and Jenny in front of him at the same time, he used his instincts and intuition to decipher who was lying between them. He realized Serena was telling the truth, because deep down, he knew Jenny was lying straight to his face. He yelled at Jenny too, “Get out!“ and it was a massive sign that he was turned off by the bleach blonde. He didn’t even want her in the same room as him.

When Jenny swiped her V-card with Nate’s best friend, Chuck.

Nate and Chuck were best friends for years, and we already saw the way their friendship was put to the test when they both had sex with Blair Waldorf in the same week. Nate felt betrayed by Blair as his girlfriend and Chuck as his best friend when that happened. It’s safe to assume Nate felt just as turned off after hearing about Jenny’s decision to lose her virginity to Chuck years later. Nate never had a chance to speak on the drama of it all because Blair swiftly banished Jenny from the island of Manhattan after all went down. However, based on Nate‘s reaction to Blair having sex with Chuck before, we have no doubt in our minds he felt just as turned off by Jenny for following the same pattern and doing something so similar. If Jenny saved her virginity for Nate, things could have turned out differently, but instead, she got in bed with Chuck and sort of ruined all of that.

What do you think was Nate‘s biggest turn-off regarding Jenny on Gossip Girl? Let us know your thoughts in the comment section below.