Nate is typically thought of as the “nice guy” of Gossip Girl. He often tries to do what’s right, he’s loyal, and he’s a good friend to the entire gang. However, with a closer examination of Nate’s role on the show, it appears that his actions are often quite questionable. From cheating on Blair to dating high school girl Sage, Nate doesn’t always live up to his nice-guy persona.
Is it possible that Nate just seems like the good guy because his wrong-doings pale in comparison to his friends’ schemes? We’ve done the hard work for you and dug up the most shameless things that Nate has ever done.
Cheats On Blair
This is famously known as one of the worst things Nate ever does since it’s a pretty prominent storyline in Season 1. The series starts off with the gorgeous and mysterious Serena returning home from boarding school, which she fled to after she got together with Nate.
Nate knew what they did was wrong, considering he was with Blair, Serena’s best friend. He continued to date Blair after Serena disappeared, but of course, Nate didn’t say a word about his cheating with Serena.
Pursues Serena
When Serena returned from boarding school she was ready to make things right with Blair. However, Nate had other plans. Even though he was still with Blair, he continued to pursue Serena after all this time. To make matters worse, Nate continued to date Blair all while secretly trying to get Serena’s attention and find time for them to “talk”.
Hate to break it to you, Nate, but there’s not much to talk about considering you still have a girlfriend. It truly makes no sense why he continued to string Blair along. Even though Nate is typically the “nice guy” in the series, he was pretty cruel to Blair for a long time.
Puts Jenny In The Middle Of His Drama
Ah, the Blair, Serena and Nate love triangle continues, simply because Nate just won’t let it go. While Nate is of course, still with Blair, he finds Serena at a masquerade ball and reveals his feelings to her and kisses her. Too bad this person wasn’t Serena, but it was actually Jenny who he kissed because apparently all blondes look the same when they have masquerade masks on.
Nate obviously felt pretty stupid about this and tried to bribe Jenny to stay quiet with a box of chocolates, which he then gives to Blair instead when she awkwardly walks in on their conversation.
Considers Giving Blair His Family Ring
Nate’s family counts on him to keep them in the Waldorf family’s good graces since they’re linked business-wise, so his mom asks him to give Blair an important family ring to prove their loyalty. The only problem is, Nate and Blair had finally just broken up and Nate didn’t want to get back together with her.
To appease his parents, Nate considers going back to Blair and giving her the ring just for his family’s sake. The fact that he would even consider taking advantage of Blair like this is pretty sickening. Luckily, he doesn’t go through with it, but the fact that he thought about it says enough.
Gets Mad At Dan For Being A Good Friend
When Dan finds out that Nate has been living alone in an empty house with just a sleeping bag, since his house was seized by the government due to his dad’s legal issues, he invites Nate over for dinner. Nate appreciates the dinner invite but when it comes time for him to leave, Dan comes clean about why he invited Nate over and asks if Nate wants to stay at the loft.
This clearly triggered Nate as he gets visibly upset and tells Dan that he has no right to get involved in his business just because they’ve hung out a couple of times. Even though Nate was probably reacting negatively out of embarrassment, he was really harsh to Dan when he was just trying to help.
Stays Friends With Chuck
Chuck has done a lot of horrible things over the course of the series, such as sexually harassing both Serena and Jenny. Considering Nate is good friends with both girls, you’d think that he wouldn’t want anything to do with Chuck.
However, Nate stays pretty solid friends with Chuck throughout the entire series and is rarely phased by the way he treats women. In fact, any time Nate is upset with Chuck it’s usually because they are simply fighting over Blair. This is all pretty strange considering Nate typically has the best moral compass out of all of the characters, but that’s not saying much.
Has An Affair With Catherine
In Season 2, we see Nate getting together with Catherine, an older woman. Not only is this not okay considering Nate’s age (he was still in high school at the time), but also because Catherine was married. To top it all off, Nate pretended to be seeing Serena all along in order to get away with this affair.
The whole situation was pretty uncomfortable and definitely made viewers wonder if this was a cry for help from Nate since, as previously mentioned, he usually has a better moral compass than this.
Dates Diana
Nate definitely has a thing for older women. Later on in the series, fans see Nate get together with Diana Payne, who later becomes his boss at the Spectator. The two were mostly on-and-off and never fully committed to one another. They also didn’t trust each other and blackmailed one another on several occasions.
It was later revealed that Diana was involved in pretty dangerous activities ,such as hiding Bart Bass who was supposed to be dead. Ultimately, this relationship made no sense and just made viewers want to scream at Nate through the TV.
Takes Down Serena’s Column
Nate didn’t get involved in the Gossip Girl drama very often, but when he did, it usually meant he was up to no good. For instance, in order to pay Gossip Girl back for a favor, he was forced to shut down Serena’s column for The Spectator.
Nate then lies to Serena about it and tells her that they’re just postponing it for the time being. Nate knew how much Serena was looking forward to the launch of her column so it was pretty hurtful that he let Gossip Girl take it away and then lied about it.
Dates Sage
When Nate meets Sage for the first time, she’s interviewing him for her journalism class since he runs The Spectator. The two start to date casually, but little does Nate know, Sage is actually in high school. While he doesn’t learn this information until he meets Sage’s dad at a gala, he continues to date her even after finding out her real age.
This is extremely strange on Nate’s part,, and it’s even more strange that the rest of the characters accept it instead of setting him straight. Luckily, Nate and Sage’s relationship is fairly short-lived but that still doesn’t make it okay.
