'Gossip Girl': The Many Men of Serena van der Woodsen
Season 1, 2, 3We all know Gossip Girl began as Serena returned to the Upper East side after she was exiled due to her exploits, namely her tryst with Nate, the previous year. The two faked a relationship in Season 2 when he was dating an older woman. They officially start dating in Episode 13 of of Season 3. They break up in the finale, as Serena is confused about her feelings for both Nate and Dan.
Source: GIOVANNI RUFINO/Warner Bros.