Serena is completely unable to be alone
Steven said it best on season 6, episode 8. "The s3x tape blew up, I broke up with her, and she ran to you because she's terrified to be alone". This 100% describes Serena throughout all seasons. And what's most annoying is that each time she is completely sure she's in love and that one is the one.
First, there was Dan. Setting aside the fact that he is peasant and she could do much better. Then they were just yo-yoing, breaking up and then getting back together. Then there was Gabriel, to whom she got "married" in a church in Ibiza. Let's not forget that weird hippie dude (Cyrus's son), Aaron. Who in addition to being weird, nasty looking hair and hippie vibes, was also allergic to commitment. Yikes. Then we have Nate (best relationship, should've been endgame, although him and Sage were a good alternative). Carter, also okay. Then, we have the creep. The teacher who expressed a romantic interest in her while she was still his student (though he never did anything with her, that doesn't make it okay). He then spent the next few years actively trying to ruin Serena's life, was clearly a dangerous dude that had Captain Archibald beat up and threatened Damien, and still she dated him. He was also extremely unfortunate looking. Finally, the other teacher S hooked up with, Colin Forrester. I did like him, but she made him quit his teaching job only to break up with him a few minutes later. Bad move.