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We Ranked All Of The Love Affairs Of Serena Van Der Woodsen - And Dan Isn't No. 1

Something that a good majority of Gossip Girl fans can agree on? Dan and Serena should not have ended up together. They were step siblings at one point, they share a half brother, and there were better people out there for both of them, but still, they ended up together. Here's a list of Serena's best (and worst) relationships.

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11. Tripp Van der Bilt

Gossip Girl, The CW / Via

Tripp was the definition of awful. First, he cheated on Maureen with his cousin's friend/ex-girlfrined, who also happened to work for him. Then, as if that wasn't bad enough he left Serena in a car crash to take the blame. Need I explain further why these two were one of the worst couples on the show?

10. Damien Dalgaard

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Sure, it was just a one night stand, but Serena and Damien were still not a good match. Simply put, Damien was an awful person and him and anyone, even Jenny Humphrey, would never be a good match.

9. Gabriel Edwards

Gossip Girl, The CW / Via–Serena_relationship

This relationship was about as confusing and unusual as they get, even on Gossip Girl. Gabriel was an awful boyfriend to Serena, considering the fact that it was all part of one of Poppy Lifton's schemes.

8. Aaron Rose

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If you take into account all of the boyfriends that Serena had over the course of Gossip Girl's six season run, Aaron Rose looks a lot better, considering what all of those other guys did (we're looking at you, Tripp Van Der Bilt). But, he still wasn't anywhere near one of her better choices. Being the son of Cyrus Rose, the best step-father a girl could ask for, makes him a little better, but consider he was dating Serena while having relationships with tons of other girls, because they weren't technically exclusive, doesn't make him that good of a boyfriend either. I think I speak for Gossip Girl's entire fan base when I say: I'm glad that Serena left him.

7. Dan Humphrey

Gossip Girl, The CW / Via–Serena_relationship

I asked myself one question when looking at how I ranked Serena's relationships: How could her husband rank so low? The only answer I could come up with was that they simply weren't meant for each other. Considering all of the factors working against their relationship, especially their shared brother, and the fact that they were step-siblings at one point, it seems like fate was trying to tell them they weren't supposed to be together. Of course, like any hard-headed couple of Upper East Siders would, Serena and Dan let fate take the back burner and continued on with the relationship and (seemingly) lived happily ever after.

6. Ben Donovan

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Ben isn't what anyone would consider one of Serena's best choices in boyfriends, and it seems she was only with him becuase of pity. But who can blame her? Her mom did forge Serena's signature to have him arrested because she thought they slept together (for any moms reading this - don't do that!). Serena and Ben were a cute idea, but them being together after her playing such a big role in his imprisonment just wasn't meant to be, and everyone could see that this relationship just wasn't going to work out.

5. Carter Baizen

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At the beginning of their relationship, I can't imagine a single person who liked the idea of Serena Van der Woodsen and Carter Baizen, but as it neared its end, I, personally, began the slow journey to loving the couple. The lengths that they went to to make each other happy were what made this one of Serena's better relationships. Her willingness to help Carter out in a time of need, and his refusal to be bought out of his wrongdoings changed opinions everywhere.

4. Max Harding

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Honestly, does anyone even remember Max? He and Serena had a short lived fling when they met in New York after he came looking for his girlfriend Ivy Dickens. Ivy was in New York pretending to be Serena's cousin, Charlie Rhodes, after being hired by Carol Rhodes, to access Charlie's trust fund. He wasn't all that bad, but he wasn't very good, either.

3. Steven Spence

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Steven wasn't necessarily bad for Serena, but I don't think there are many Gossip Girl fans who would say that they wanted this couple to end up together, either. The two biggest flaws with this relationship were Sage, Steven's daughter, and his past one night stand with Lily, Serena's mother. Sage's daughter's schemes to break up her father and the socialite caused many problems within the relationship, and her relationship with Serena's friend and ex-boyfriend, Nate Archibald didn't help either.

2. Nate Archibald

Pat Harbron / THE CW, GOSSIP GIRL --"High Infidelity" --,image GO602A_0338 Pictured (L-R): Blake Lively as Serena Van Der Woodsen and Chace Crawford as Nate Archibald -- Photo: Pat Harbron/The CW -- © 2012 The CW Network. All Rights Reserved. / Via–Serena_relationship

Serena and Nate were just two characters that were seemingly meant to be together. They fit perfectly, with similar laid-back attitudes (or at least as laid back as a teenage socialite can get).

1. rColin Forester

Gossip Girl, The CW / Via

Honestly, does Colin Forrester have any flaws? Okay, yes, I know what you're probably going to say; "his cousin (Juliet Sharp) drugged Serena and left her for dead in the back of a limo, and he's her professor!"

But, to be fair, he was willing to quit his job to be with her - how sweet!

The family problem, though, is a hard one to spin in any way that would work out. But, Colin, as a person, was a great match for Serena. An attractive, older, bachelor. If it wasn't for the fact that his cousin Ben dated Serena, and Ben's sister Juliet tried to kill her, they would make a perfect couple.

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