Ahh Serena van der Woodsen. Infamous for dating one inappropriate guy after another. But in the ocean of regrettable relationships, they were a few good guys in the mix. So here is a ranking of all of S’s boyfriends, ranked worst to best.

7. Dan Humphrey

Lonely Boy should have remained lonely and did not deserve S in the end, IMHO. He was rude, judgmental and honestly a huge hypocrite. In the beginning he judged without even knowing her, then he abandoned her when she needed him the most. Then he went and slept with Georgina, Serena’s nemesis. And to top it off, he dated her best friend while he knew she was still in love with him!!! As if that wasn’t despicable, he even wrote and published an expose on her and called her shallow and superficial!!! I think he is as bad as it gets.

6. Gabriel Edwards

Now this relationship put Serena in a sticky situation. Instead of taking S’s heart, Gabriel took her money instead. This ponzi scheming guy deserved to be with the likes of Poppy Lifton and Serena could do wayyyy better.

5. Steven Spence

This relationship just had to spark. Sure he was mature and stable but there seemed to be zero love. After all Serena was closer in age to Steven’s daughter Sage than to Steven. This seemed to just be a palate cleanser.

4. Aaron Rose

Now here’s a guy who can’t appreciate a beauty when he sees one. Not only did he cheat on his previous girlfriend, but he refused to break up with her when he started seeing Serena. Sharing is caring but it has its limits…

3. Trip van der Bilt

Here’s a case of horrible timing. Although these two forbidden lovers cared for each other, complications like a wife, political campaign and family legacy came in the way. While Trip didn’t deserve Serena (he did leave her injured in the middle of nowhere and ran off to save his own reputation), there was a time when he did truly care for her.

2. Ben Donovan

This was one cursed relationship. Serena finally fell for a guy who had integrity and stood up for her, but this relationship just wasn’t meant to be. Ben truly did deserve happiness after his jail stint (for no fault of his) but modern day aristocrats don’t seem to take to well to ex-cons (although Ben was innocent!). Also there was that whole awkward situation where he tried to ruin her life…

1. Nate Archibald

THIS IS WHO SERENA WAS MEANT TO END UP WITH! Finally a guy who can understand her life!!! Nate was hopelessly in love with Serena ever since season 1 and when they finally got together, their relationship was beautiful. They understood each other perfectly and had so much fun. No matter who she ended up with in the show, Serena and Nate will always be my OTP.