Gossip Girl wrapped up in December 2012, yet fans of the series are still not over the iconic show. Combining romance, drama, occasional humor, and eventful plot twists, “the scandalous lives of Manhattan’s elite” are always worth celebrating.
So, whether you’re still not over Blair Waldorf (Leighton Meester) and Chuck Bass’ (Ed Westwick) toxic relationship or are still wishing the spinoff prequel about Lily van der Woodsen (Kelly Rutherford) had become a reality, this is the place to air out all your grievances — especially the romance ones.
This time around, however, we’re focused on the worst match of the series — Serena van der Woodsen (Blake Lively) and Dan Humphrey (Penn Badgley). The couple had nothing in common. They were never the right fit for each other, especially when you look back at her other romances. While there’s nothing that can be done now, it’s still fun to speculate who could’ve been a better match.
Scroll down below and see which ex-boyfriend of Serena would’ve been the best pick, according to Swooon.
Giovanni Rufino / The CW / Everett Collection
5. Aaron Rose
Okay, Aaron Rose (John Patrick Amedori) is not nearly as lovable as his father, Cyrus (Wallace Shawn), but he was still a somewhat decent match for Serena. Sure, his faux intellectual stance on monogamy was annoying, and his creative pursuits were questionable at best, yet he was still better for Serena than Dan. The budding couple only served one purpose in the series: to get Dan to realize that Serena was the one for him. But all it did for the fans was showcase how Serena needed some time without a lover by her side.
No, she and Aaron would’ve never lasted in their youth, but am I the only one who sees that they could’ve worked if they rekindled as more mature people?
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4. Steven Spence
Was the relationship between Serena and Steven Spence (Barry Watson) a bit odd? Yes, for sure. He was way older than her, and Nate (Chace Crawford) was simultaneously dating his daughter, Sage (Sofia Black D’Elia). Talk about weird, am I right?
He did, however, have the right attributes that kept Serena on her toes. Steven was equally dominant and caring. The CEO also had a manipulative side, which popped out when he tried to win Serena back. These would’ve been red flags for anyone besides Serena, but the socialite had some conniving traits as well. He gets marked down because he did have a one-night stand with her mom, Lily, and that was just too weird for me.
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3. Colin Forrester
Serena does really love her an authority figure. After sharing a crazy night with her psychology professor at Columbia, the two tried to take a break but just couldn’t resist each other. Who doesn’t love a forbidden romance? Still a somewhat controversial relationship, Colin Forrester (Sam Page) was a catch. He respected Serena, and their chemistry was sizzling.
The only real issue they encountered, besides the whole pesky professor-student thing, was Juliet Sharp (Katie Cassidy). Juliet was his cousin, and he supported her financially. She had a vendetta against Serena and almost broke them up. Juliet didn’t succeed, but Colin and Serena ultimately split anyway. Luckily, on their own terms.
Nate’s one true love will forever and always be Serena. They could have been the perfect golden retriever couple. Not as calculated as the rest of their pals, this duo would’ve been one for the ages.
From the very first episode, it was apparent that Nate was head over heels in love with Serena. His googly eyes for the blonde bombshell never ceased. Although the two tried to make it work on several occasions, it was Serena’s lack of therapy that made this couple fail. She was still too attracted to guys who were wrong for her, and that’s why she wasn’t able to see the person who was actually perfect for her: Nate. They could have ruled New York City
Plenty of people use the line, “opposites attract,” but sometimes that just doesn’t work out. Do you know who would? Characters with the same personality. Serena and Carter Baizen (Sebastian Stan) were cut from the same cloth. They were each other’s perfect match. They were neither inherently bad nor good, spoiled by their privileged upbringing, believed that the world was easier than it actually is. These two always saw each other for who they truly were — and they never wanted to change the other. (Unlike Dan.)
A lasting relationship between Serena and Carter would have meant that both parties always had someone they could rely on. The two also had an undeniable chemistry that was palpable whenever they shared the screen together. Carter and Serena should have been endgame!