Over the years, there were so many juicy relationships featured on Gossip Girl, and one of the characters who seemed to rack up the most kisses, girlfriends, and hookups was Nate Archibald. He was the all-American boy. He was charming and athletic. And he certainly had a way with the ladies!
While he was associated with some high-profile and beautiful women on this teen drama, not all of his significant others were good news or good matches, necessarily. In fact, there are a few that many viewers would surely pass on, as well, (since they could lead to disasters)... but there are definitely some exes that fans would love to get with, too!
Date: Blair Waldorf
At the beginning of this TV show, Nate and Blair Waldorf were the it couple. They both came from well-known and well-off families, they both had preppy styles, and they both seemed to be a match made in heaven.
The relationship hit some bumps in the road, and neither of these characters were even close to perfect. Still… Blair would be a great girlfriend, with her romantic personality and stylish beauty. Plus, she came with drama, which, on the bright side, just added some spice to things!
Disaster: Catherine Beaton
One summer, Nate began an affair with a woman named Catherine Beaton. She was married to a lord, and she had a stepson named Marcus… a stepson who was dating Blair and who was also having an affair with Catherine!
This was messed up on so many levels, so for many, the answer here is pass.
Date: Serena van der Woodsen
Nate cheated on Blair with her best friend, Serena van der Woodsen, and then these two tried to give it a go; they had been friends for years, and they were both super attractive, so it made sense.
It may have not led to a happily ever after, but Serena was a blonde it girl. She was fun and feisty. She was sweet and loving. She was attractive and from an affluent family. Dan was a lucky man!
Disaster: Juliet Sharp
Another one of Nate’s exes was Juliet Sharp. They both went to Columbia, and upon first impression, she seemed like a real winner. Looks can be deceiving, though, and Juliet was just trying to get close to/takedown Serena, since she blamed S for putting her brother, Ben, in prison.
Family baggage can be a lot to deal with, especially when it comes with a need for revenge, so this would be another no-go for many fans.
Date: Vanessa Abrams
Vanessa Abrams was friends with Dan Humphrey for years, and she did not love the idea that he was becoming part of the Upper East Side. Yet she found herself getting involved with a couple of men from this glam world, including Nate. Both easygoing and genuinely nice people, this couple could have worked out and made it all the way.
They did not, of course, and things went south with Vanessa overall. Surely she forgave herself and was forgiven by this group, though, because her bright and creative vibe was something to love, for sure.
Disaster: Ivy Dickens
Everyone remembers when Ivy Dickens was around, pretending to be Serena’s cousin. She fooled all the main characters in a variety of ways, including tricking a few men into kissing her (or more). Yes, Nate had a moment with Ivy, before he realized who she really was and what she was doing in their world.
Lying, getting close to people then hurting them, only caring about money… The list goes on and on, when it came to reasons not to be with or like Ivy!
Date: Lola Rhodes
On the other hand, Serena’s actual cousin, Lola Rhodes, showed up and started dating Nate, and these two also seemed so great together! While she ended up leaving the Upper East Side, it was easy to imagine them getting back together in the future.
Lola did not grow up in a world full of materialism, so she had an authentic sweetness to her. She was also a go-getter who knew what she wanted in life, was not afraid to speak up/out and was chasing her dreams.
Disaster: Diana Payne
Obviously, Nate had a thing for older women, because he got involved with Diana Payne, as well. She only cared about her newspaper, The New York Spectator, though, so she set Nate up again and again and even turned out to be working for his grandfather behind his back.
She may have been powerful and pretty, but a relationship should come before everything else… including lies and backstabbing.
Date: Jenny Humphrey
For years, Jenny Humphrey had a crush on Nate, and when he became friends with Dan, he saw her as a little sister. Until things changed. These characters shared a couple of steamy moments before Little J was run out of town.
When Jenny was shown in the final episode, she seemed put together, grown-up and much better. After she dealt with her issues and matured, she could have been a really good girlfriend and friend in general.
Disaster: Raina Thorpe
There were several other women Nate kissed and dated, such as Raina Thorpe. She was another attractive and strong female character, but her father was trying to take Bass Industries away from Chuck. Therefore, dating her came with complications.
She may have been much better than some of the others listed out here today, but anyone who was involved in hurting Chuck more was not someone worth dating.