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If there’s a sympathetic character in Gossip Girl, it’s Nate Archibald. Although he was rich and privileged, he was the least malicious of the main group, seemed to actually care about people, and rarely involved himself in the schemes that the rest of his friends did unless he truly thought it was the right thing to do.
RELATED: Gossip Girl: 5 Times We Felt Bad For Serena (& 5 We Hated Her)
Despite fans feeling bad for Nate so much of the time due to a generally good nature though, he did have his bad moments — like everyone. Fans might have spent most of the series feeling sorry for him, but there were a few moments where they hated him too.
10 Felt Bad: When His Father Was Imprisoned
Nate’s father gets into quite a bit of trouble and ends up imprisoned, which leaves his family strained. Nate tries to visit his father and have a good relationship with him, since he turned himself in like Nate asked, but it’s still a painful time for Nate. He’s only a teenager and he barely sees his father, as well as having an extremely damaged family reputation after all that.
9 Hated Him: Slept With Serena
Before the series even began, Nate slept with Serena.
Why was this terrible? He was dating her best friend.
He remains very in love with Serena throughout a lot of the series, but it’s still completely appalling that he gave into temptation and slept with her while he was with Blair. Serena was so ashamed of herself she ran off afterward, and Nate did his best to hide it from Blair.
8 Felt Bad: When Blair Was Clearly In Love With Chuck
After Blair finds out and they mend their relationship, Blair is so clearly in love with Chuck that it’s painful. She tries to stay with Nate because he seems like the right choice, but the chemistry between Blair and Chuck is tangible. Despite what Nate has done in the past, it’s still painful to watch him struggle with his girlfriend having strong feelings for someone else, especially as his father pressures him to stay with her because of who her mother is.
7 Hated Him: Messing Around With Jenny
Nate has a brief, strange thing with Jenny and it’s… just weird.
Jenny is in a bad place at that point and is also a little young for Nate considering their stages of life. The decent thing to do would have been to have been there for her as a friend, but instead he actually pursues something romantic with her. It’s not something most fans ended up shipping.
6 Felt Bad: When Blair Slept With Chuck
When Nate finds out that Blair has slept with Chuck, he’s devastated. It’s a bit of a grey area, considering she wasn’t exactly cheating, but Chuck is his best friend and it’s a betrayal on both parts. When Nate and Blair get back together, Blair attempts to hide it from him but he finds out anyway and his pain is clear.
RELATED: Gossip Girl: 5 Times We Felt Bad For Chuck (& 5 We Hated Him)
At least he knows how Blair felt when she found out he slept with Serena.
5 Hated Him: Helping Ivy
Charlie, Lola, Ivy… Quite a whirlwind Nate gets himself involved in, considering he falls for Lola who is actually Charlie and ends up helping the fake Charlie, Ivy. Hard to keep track.
He’s manipulated into going into the safe in Lily’s apartment and retrieving Bart Bass’ files on the whole family, which is a pretty unforgivable betrayal. Especially as he hasn’t known Ivy that long and has no way to verify that her intentions are good.
Which they aren’t.
4 Felt Bad: When He Was Pretty Much Homeless
At one point when his father is imprisoned, Nate ends up pretty much homeless. He has nothing left and tries to hide the fact he’s lost all of his wealth from his friends out of pride, despite knowing they would help him. It’s heartbreaking to see someone think that their wealth matters that much to their friends and refuse to ask for help.
3 Hated Him: Snapping At Dan
In a surprising twist of events, Dan is the one who tries to help Nate. He finds out about his situation, tries to befriend him properly, and invites him to stay over.
Initially, though, Nate’s privileged pride kicks in hard and he refuses Dan with some really harsh words about how they aren’t actually friends. Ouch.
2 Felt Bad: When He Was Being Blackmailed
Nate gets money to keep his family afloat by sleeping with a rich older woman, who ends up being seriously controlling over him. Nate sees no way to break away from this considering she knows where his father is hiding out before he’s in prison, and it’s a sticky situation for someone to be in. Especially someone so young and keeping his whole family afloat.
1 Hated Him: Lying To Vanessa
At this point, Nate is dating Vanessa and the two of them seem to be doing really well — however, he’s lying to her about the older woman. Eventually, she sees them together and draws the logical conclusion that he’s cheating on her, just about breaking her heart.
Communication isn’t his strong point.
NEXT: Gossip Girl: 10 People Nate Could (Or Should) Have Ended Up With
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Staci is a politics/psychology graduate from Scotland who went on to work in neither of those fields in the end. It happens. She’s a freelance writer who contributes to various Valnet sites and, when not working or travelling, spends most of her time watching horror movies, wasting an unreasonable amount of hours on the PS4 (despite being a Nintendo girl at heart), and trying to force her cat to love her.
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