Summary

• Serena's love life on Gossip Girl was complex, with boyfriends ranging from con artists to best friends to former teachers.
• Her significant others didn't just come from her social circle but also from her travels, adding to the drama of her romantic life.
• Serena's relationships were filled with lies, scandals, and manipulations, but some boyfriends showed genuine care and support.

Serena van der Woodsen was a true icon on Gossip Girl, with a dating history of boyfriends that was just as complicated as it was exciting. Since the dissolution of her relationship with Dan in season 1, she has dated a plethora of men, some of whom included her childhood friends, former teachers, con artists, politicians, and then Dan (again).

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When she wasn't looking for Gossip Girl's identity or charting her own unique path in a world of privilege and traditions, her love life was a major point of her story on the show. Like most other teens on the Upper East Side, Serena kept a swiftly revolving door of partners, and she liked to mix things up. Serena van der Woodsen's significant others in the series weren't just those in her tight social circle but included people she met in her travels and some characters who only stayed for a handful of episodes before they moved on.

10 Tripp Vanderbilt

Played By Aaron Tveit

Serena and Tripp started having feelings for each other while she was working on his campaign, but the problem was that he was married. Tripp tried to keep Serena as a mistress while the Vanderbilts stayed married, but Serena didn't want to be involved in any of it.

Tripp was an awful partner because he lied to Serena, tried making deals with his wife without her knowledge, and then eventually left her in a car accident to die when he realized that getting caught would harm his reputation. He had no humanity whatsoever and Serena deserved better.

9 Gabriel Edwards

Played By Armie Hammer

Some fans might not even remember that Armie Hammer played one of Serena van der Woodsen's boyfriends in Gossip Girl. While on vacation with her friend Poppy, Poppy's boyfriend Gabriel left Poppy for Serena and followed her to New York. Poor Serena didn't know better than to recognize all the red flags and got swept away in the exoticism of European vacations and sudden romance.

Unfortunately, the entire relationship was a scam, and Poppy Lifton was revealed to have been in on it from the beginning. What began as a ploy to get some money off of Serena's moneyed network became way too complex, and even though Gabriel did seem to have genuine feelings for the golden girl, he was too shady at the heart of it. This was one of the saddest things to happen to Serena, who was naturally trusting.

8 Aaron Rose

Played By John Patrick Amedori

In season 2, Serena started dating Aaron Rose, seemingly for something to do. He was a pretentious artist-type who took pictures of beautiful women but couldn't bring himself to commit to monogamy. This clashed hugely with Serena's dating style. Though she'd had multiple partners in the past, that wasn't something she wanted anymore.

The only emotion he showed was mild annoyance when Serena dared to assume that they were exclusive before he decided that they were. The relationship was quite inconsequential, as he only served as a bargaining tool for Serena to try to get Dan to admit he still loved her.

7 Max Harding

Played By Brian J. Smith

Season 5 saw Ivy impersonating Charlie Rhodes, but her disgruntled boyfriend made it back to New York to haunt her, and to use Serena as bait. Max seemed like a sweet young man but became spiteful soon after, as often happened with the Serena van der Woodsen significant others who got a crash course in the Upper East Side. It was obvious that his agenda was to get in on the wealth of the UES crowd, and like many others, he used Serena as an in.

The two dated very briefly, but broke up when Ivy made everyone believe that he was a liar. The unpopular opinion was that Serena was too naive to know better, but Max took advantage of her to blackmail Ivy, which made him a pretty terrible person. Despite Serena knowing how manipulative those in her social circle could be, she always seemed to trust those with a romantic interest in her.

6 Ben Donovan

Played By David Call

Ben was Serena's teacher when she was a boarding school student (and a minor). The two had feelings for each other, but never acted on them. Though nothing physical ever transpired between them, Lily forged an affidavit accusing him of statutory rape, but this bit her later on when Ben and his sister, Juliet, hatched a plan to ruin Serena's life.

When Ben was released, he and Serena started a legal relationship. Sadly, there was no time to unpack the creepy origins, the trauma of being falsely accused and sent to prison, or the fact that his sister drugged her and set her up. The two dated pretty briefly before it became clear that the relationship was too complicated to go anywhere. Ben was both Serena's ally and a threat to her during his brief time on the show.

5 Dan Humphrey

Played By Penn Badgley

Dan Humphrey is the best-known of Serena van der Woodsen's boyfriends because their on-again-off-again romance defined much of their time in Gossip Girl. Dan and Serena started dating early on in season 1, but complications like Georgina, their differing social statuses, and sharing of half-siblings made their relationship extremely messy. Dan couldn't accept many of her personality traits, which made fans feel bad for Serena.

Despite their hang-ups, Dan and Serena's love persevered, even when Dan was very much in love with her best friend Blair. He could be loving and supportive, but his moments of jealousy and wavering loyalty proved to be problematic. Still, it was clear that they were meant to be. Despite Dan being revealed as Gossip Girl and torturing Serena for a better part of 6 years, she said she understood him and forgave him before they ended up together in the finale.

4 Colin Forrester

Played By Sam Page

Serena met Colin Forrester by chance, but they hit it off almost instantly. Things were made complicated by the fact that he was her professor, but Colin did seem interested enough in her to quit his short stint as a guest lecturer to be with her. He was genuine and helpful, but his fault was bad timing.

The two broke up soon after, mainly because this relationship came in the middle of the Dan vs. Nate debacle. Serena couldn't choose between the two men in her life, so she used Colin as a distraction which made this romance fizzle out quickly. He's not exactly the most memorable of Serena van der Woodsen's significant others as a result.

3 Steven Spence

Played By Barry Watson

Being the main character was Serena's job, but it got exhausting. After running away from Manhattan, she met Steven and pretended to be someone else. However, he was mature enough to realize Serena's demons, and accepted her wholeheartedly, despite the false pretenses under which their relationship began.

Sadly, the Upper East Side and his teenage daughter Sage had other plans for the couple. Sage tried to sabotage Serena at every step and succeeded when she released her sex tape. Steven was a decent man who wanted Serena enough to propose to her, but the drama eventually got to him, and he broke it off.

2 Nate Archibald

Played By Chace Crawford

Nate and Serena seemed like star-crossed lovers when Gossip Girl began, but their romance was just a teenage dream. Nate, who always had a thing for Serena, stood by her through every awful choice she made with his cousin Tripp and the aftermath of the accident, which made them realize they wanted to be together. He seemed like he would have been the perfect final boyfriend for Serena van der Woodsen, but the show had other plans.

Nate had a pure soul, and he always wanted the best for Serena. Nothing could retrain his focus from her, not even Jenny, but Serena left him behind when he called the cops on William for giving her fake cancer. He had the best intentions but played his cards wrong. Unfortunately, Serena's fondness for Dan ultimately put an end to her and Nate's relationship.

1 Carter Baizen

Played By Sebastian Stan

Serena and Carter were actually pretty well-suited to each other: both had scandalous pasts and weren't particularly trustworthy, but were trying to be better people than others gave them credit for. Carter showed up for her when she was struggling with her father and trying to find answers, and he helped her emotionally, which was something nobody else ever did for her.

Carter was a worthy partner because of how self-aware he was. He never harmed Serena and tried to make her feel better at all given points. If his past hadn't come back to haunt him, he may have been her ideal partner, and they could have finished Gossip Girl together.