Despite being a teenager during pretty much the entire run of Gossip Girl, Serena van der Woodsen had her fair share of romances. Well, every character in the show certainly managed to date around — despite their ages and time constraints — but Serena was especially prolific.
Ultimately, she ended up with Dan Humphrey — as we all knew she would. Of course, this makes absolutely no sense: he was a creepy stalker who had lived a double life the whole time they knew each other, with him attempting to ruin her life on multiple occasions. Here are 10 possibly more realistic options for who Serena could have ended up with.
10 Nate Archibald
At the very start of Gossip Girl, Nate was in a relationship with Blair Waldorf. Things seemed to be going rather well for the pair of wealthy Upper East Siders, but Serena had a secret: she and Nate had slept together.
This suggests that there was obviously a bit of chemistry there. Nate and Serena ended up together on a couple of occasions, actually. Add that to the fact that Nate was the only character in the show who was truly nice, and maybe Serena should have pursued him a little more.
9 Aaron Rose
In the second season, we are introduced to Aaron Rose, an edgy artist with an alluring, arrogant attitude. His demeanor seems to draw Serena in, and she becomes rather obsessed with him before finding out he is the son of Blair’s stepfather, Cyrus Rose. They also find out that they used to knew each other, and had a fake wedding as kids. Cute. The two ended up together for a while, but their romance was marred by Serena’s love for Dan, and Aaron obviously noticing the elephant in the room. Would Serena have been better off with her childhood sweetheart?
8 Gabriel Edwards
Another of Serena’s Season 2 flings, Gabriel was rather short-lived. A twist-heavy, drama-filled storyline in which the two begin to date, ends with Serena finding out he is still seeing Poppy Lifton behind her back. Plus, there’s the revelation that Gabriel is a con man, gaining investment with no plans to use the money for good.
However, Serena still seems interested. Gabriel ends up redeeming himself very slightly, explaining that he actually did like Serena. It seems unlikely, but we wonder what might have happened should Serena have not decided to avoid him from then onward.
7 Carter Baizen
Despite the fact that Carter Baizen seems like an important, central character in Gossip Girl, he only appears in eleven episodes. This is enough time for him to enter into a relationship with Serena, though. At first, the two are engaged in a strange mission to find her father. Then they have sex in the woods. Then she pretends to want a relationship. Then she actually wants a relationship. Then they break up. It’s all a little confusing, but it could have ended up going somewhere if Serena hadn’t been so wishy-washy.
6 Ben Donovan
Despite only being introduced in Season 4, Ben Donovan has a remarkable influence and importance in Serena’s past life. It transpired that they had a relationship while he was her English teacher (Pretty Little Liars, anyone?), making him, in effect, a sex offender. It’s all a little weird, but if they didn’t have such creepy, illegal history, and Serena met Ben when she was an adult, then perhaps things might have worked out.
5 Steve Spence
GOSSIP GIRL, from left: Blake Lively (carrying a Bottega Veneta handbag), Sebastian Stan, ‘The Lost Boy’, (Season 3, ep. 303, aired September 28, 2009). 2007-. photo: Giovanni Rufino / © The CW / Courtesy Everett Collection
Let’s just try and remember how young Serena Van Der Wooden is supposed to be in Gossip Girl. In the first season, she is still in high school, and by Season 6, only a couple of years out. This makes it pretty strange when she ends up in a relationship with the much older Steve Spence. In fact, the two very nearly ended up married.
Serena, as you might have expected, ends up returning to Dan, and explains this to a disappointed Steve over dinner. When Serena breaks up with Dan (for the ten billionth time), she tries to call Steve, but he doesn’t pick up. What could have been.
4 Tripp Van Der Bilt
In a strange, unrelatable dynamic, Tripp is his cousin Nate’s main competition for the affection of their shared . Despite Tripp’s wife having filed for divorce against him, he has time for a quick affair with Serena which doesn’t really lead anywhere. It might have been a bit of strange relationship anyway, what with Serena’s history with Nate. But at least Tripp didn’t blab about Serena’s personal life all over the internet.
3 Colin Forrester
Colin Forrester was a recurring character in Season 4. He was a billionaire and a guest lecturer at Columbia, and Serena took a shine to him rather early on. The two ended up pausing their relationship until the end of the semester when they were no longer teacher and student, but their failed attempts to do so were caught on camera. They ended up breaking up with no hard feelings, but Colin wasn’t a bad guy, so it could have worked.
2 Max Harding
Most viewers probably don’t really remember Max. He emerged during that weird period in which Ivy and Charlie co-exist but one of them is pretending to be the other, remember? Anyway, Max and Serena kiss, then go on a couple of dates.
He is being paid for his involvement in all of this, but his feelings toward Serena seem real. After his last scene on the show, Serena seems to regret her actions when she realizes he was telling the truth about Ivy/Charlie the whole time.
1 Chuck Bass
Despite Chuck Bass’ incessant desire to flirt and sleep with just about every person he has ever laid eyes on, he and Serena never end up together. This isn’t through lack of trying on his part, but she constantly rejects him. And then they sort of end up as siblings, so this is probably for the best. Then again, she and Dan are effectively related as well. Maybe Chuck would have been more her speed.
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