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All Of Nate Archibald's Flings Rated

Nate has a problem with bad relationships, and a few of them involve much older or much younger women - for example: Sage Spence, Jenny Humphrey, Catherine Beaton, and Diana Payne. And if they're not way out of his age range, then they're probably hiding some huge deal-braking secret. Or maybe both. It is Gossip Girl we're talking about, and secrets and scandals are basically the entire plot line of the show.

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12. Diana Payne

Gossip Girl, The CW

There wasn't a single thing that wasn't wrong about Nate and Diana's relationship. Other than the fact that it was thrilling to watch, this was hands down Nate's worst choice in a girlfriend (and there are 12 of them on this list). She was using him in her schemes, and even scheming against him at points. She was (possibly) the mother of his best friend. She had a one night stand with his best friend's dad. And she also happened to be way older than him - but Nate tends to lean towards older women, so maybe that one wasn't exactly her fault. Either way, there were no redeeming qualities in this relationship.

11. Juliet Sharp

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If Juliet's motive in dating Nate hadn't been to get close to his friend (and ex) and leave her for dead in a limo, this relationship could have been, like, number five. But since Juliet was kind of really evil, she brings this relationship down to the second to last on the list.

10. Duchess Catherine Beaton

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Another one of Nate's older women, Catherine was an interesting case. The fact that their relationship was an affair based on lies (from both parties) made it bad enough. Once you find out that Catherine Beaton is actually the lover (and step-mother) of Nate's ex girlfriend (and friend) Blair's boyfriend, Lord Marcus Beaton, this entire relationship loses any of the appeal it may have had.

8. Jenny Humphrey

Gossip Girl, The CW / Via–Nate_relationship

Jenny's crush on Nate was cute - until it ruined his even cuter relationship with Serena. For a second it was cute when they got together, too. But Jenny's role on the show was basically just being annoying and ruining perfectly good things (like Serena and Nate's relationship)

7. Sage Spence

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Sage and Nate were a cute couple in theory, but the factors that go into every relationship in Gossip Girl are what ruins it. Sage being the daughter of Nate's ex (and friend) Serena's boyfriend/fiancée kind of puts a damper on things. Follow that with the fact that she was scheming to the likes of Blair (okay, maybe not that well), she just wasn't the right girl for Nate.

6. Bree Buckley

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The Romeo and Juliet-esque nature of Nate's relationship with Bree Buckley was adorable. Of course, the fact that it didn't last because of this was - while inevitable - fairly upsetting. Bree also had a few skeletons in her closet that make her one of Nate's lesser relationships.

5. Raina Thorpe

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A lesson everyone can take from Nate and Raina's relationship: You probably shouldn't fall for the girl your best friend likes (especially while you're trying to get her to go out with him).

4. Lola Rhodes

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Lola makes one half one of Nate's least-complicated relationships. Outside of their relationship, the complicatedness of Lola's life is through the roof, but what Nate and Lola have is something special. Especially since Lola is one of the first girls Nate has actually had to work for. Lola's sweet and down-to-earth personality is a great match for Nate.

3. Blair Waldorf

Gossip Girl, The CW / Via–Nate_relationship

Blair and Nate had a wonderful relationship. The two flaws that stood in the way of their life as the perfect Upper East Side power couple: Nate's affair with Serena at the Shepherd wedding, and later: Blair's feelings for Chuck, and their affair in the back seat of a limo. Ultimately, this relationship was doomed from the pilot, but it was cute while it lasted.

2. Vanessa Abrams

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Nate and Vanessa were from two different worlds. Ultimately, unlike Dan, Vanessa couldn't adapt and work her way into the life of an Upper East Sider. Although this short lived fling was adorable, there was no way it could have lasted.

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