Serena Van Der Woodsen is a socialite of the upper east side and the most featured character on "Gossip Girl." Although the way that she lived her life was very reckless and dramatic, we all wanted to be her. The television series would not have been the same without her many relationships with men.

From Brooklyn writers to millionaire professors, Serena made her rounds before settling down with the right one. Although she made a few questionable choices, she dated some very eligible bachelors. From the worst to the best, here is the definitive ranking of Serena Van Der Woodsen’s boyfriends.

9. Ben Donovan

Is it even necessary to explain why he is ranked last? After he and his sister, Juliet, tried to ruin Serena’s life, we forgave him for the misunderstanding, but then he was the reason Lily was sent to jail.

8. Aaron Rose

He was never Serena’s type from the beginning and when he tried to have an “open” relationship, we knew he was doomed.

7. Gabriel Edwards

Serena deserves more than Poppy Lifton's sloppy seconds. That is why this relationship was short-lived.

6. Steven Spence

This relationship brought out the maturity in Serena, which viewers loved. Unfortunately, it was way too complicated. Between Steven’s daughter hating Serena for having a history with her boyfriend and Steven sleeping with Lily years before, the two were not meant to be.

5. Tripp Vanderbilt

Forbidden love and Serena as a mistress was all fun and games until Tripp left her in a crashed vehicle. The relationship never really felt right anyway, since all that you could think about the entire time was how Serena should be with Nate.

4. Carter Baizen

Although he is an enemy to some, we cannot dislike him as a companion to Serena. Although they had their fair share of drama, he was the one who found Serena’s father.

3. Dan Humphrey

As frustrating as it was that Serena could be attracted to a Brooklyn boy, the relationship that Dan and Serena shared was cute because it overcame all odds.

2. Colin Forrester

This was the better of Serena’s two relationships with professors without a doubt. He was intelligent, a millionaire, and he was gorgeous. He was the perfect man for Serena and he never did anything to wrong her.

1. Nate Archibald

It does not matter who Serena married at the end of the series or how many boyfriends she had along the way, she belonged with Nate. Nothing can beat their history and the adoration that he has for her. The two of them not ending up together is the one thing that "Gossip Girl" messed up on.