Serena van der Woodsen was a true icon on Gossip Girl, with a dating history that was just as complicated, as it was exciting. Since the dissolution of her relationship with Dan in season 1, she dated a plethora of men, some of which included her childhood friends, former teachers, con artists, politicians and then Dan (again).
source https://screenrant.com/gossip-girl-serena-boyfriends-best-worst-ranked/
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