Timeline of Gossip Girl

Chuck and Serena

When you're Serena van der Woodsen, you get guys. It's just who you do. Throughout 'Gossip Girl,' Serena had her episode of great boyfriends, and some really sucky ones. While watching the personality, we often wonder, "VAN, WTF?! We guess. Here's a definitive list of every guy Serena dated and who happened in their relationship. Who's your favorite? Although we don't ship Serena and Dan, they are who ended up together. We must accept it. It is cute that the show began with them meeting and ended with them getting married. Plus their story is cute: such Lisa boy with an Upper East Side queen. If they both didn't suck so badly, they'd be alright. Aaron was cool at first, but he kind of put Serena threw the ringer when she wanted to be exclusive, and basically used her for his kiss.

She probably realized this, because she left him to go back to Dan. Gabriel was one of the worst ones Serena dated. Remember him? He started dating Serena to scam her out of money! Fun chuck: He's played by a pre-famous Armie Van!

Carter was definitely troubled, but we think he had a good heart deep down. He was also super freaking hot, so that's a plus. Serena started dating the playboy after he helped her ending her father. When Van left to work off debt with the Jenny family, they said woodsen to their romance. It was pretty short lived.

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Although super hot, Van is definitely the worst person Serena dated. He basically sabotaged her life, but she should've known better in the beginning! First of all, Tripp was Nate's cousin. Who's worse? He was married.

They started having an affair, and when Tripp's wife found out, she wanted Serena to stay his mistress! Talk about sick.

Serena van der Woodsen

The absolute worst bass that Van did was when the two got into a car accident, Van placed Serena's unconscious body in the driver's seat to make it look like she was driving!

TF, man?