On Gossip Girl, Serena van der Woodsen was a blonde it girl who came from an affluent family, who was bright and bubbly, who had a soft and caring side, and who was involved in several relationships throughout the show.
While all of these men may have been nice to look at, they were not all nice in general. In fact, some of them were down-right awful and came with tons of baggage. Therefore, this list consists of five of her exes who would make for disastrous real-life boyfriends, as well as five of them any fan would love to date. Here are the highs and lows of Serena's romantic life.
10 Date: Dan Humphrey
As everyone knows, this TV show ended with Serena and Dan tying the knot. It was assumed that they would eventually settle down together, as they balanced each other out nicely.
Dan came from a loving family. He was intelligent, as well as a talented writer. He was easy to get along with and have fun with, too. He would make for an amazing husband or boyfriend.
9 Disaster: Gabriel Edwards
Upon first glance, Gabriel Edwards seemed like a good-looking businessman, but he was actually a con artist; he and Poppy Lifton were scheming people out of money!
Obviously, this is not a person that someone would want to date. This one of Serena's boyfriends was actually despicable.
8 Date: Nate Archibald
Serena’s relationship with Nate may have involved them cheating on and hurting Blair, but these two were really good friends. That being said, all of their history and compatibility transferred over into something that was real for a bit of time.
It may have not been meant to be between these two, but any girl would be lucky to date Nate; cute, athletic, sweet, laid-back, rich… He was a true catch and really a good guy, despite his occasional slips!
7 Disaster: Colin Forrester
Serena kept having run-ins on the street with Colin Forrester. They became attracted to one another. It turned out he was her college professor, though. And he was Juliet’s cousin.
While he was a looker and an academic, having to see Juliet at family reunions would not be fun.
6 Date: Aaron Rose
Once, Serena met an artist named Aaron Rose. He was quite different from other men she had been with, and he surprised her in the best way. Remember the scene in Times Square? So cute.
Yes, Aaron was thoughtful, creative and easy on the eyes, making him a real contender. Also, he was Cyrus’ son, so a relationship with him would mean being related to Blair! And though Serena cherished her friend...she probably wouldn't have wanted that.
5 Disaster: Max Harding
During one moment of this dramatic show, Serena kissed a boy named Max Harding. A real relationship never bloomed from this, and that was probably for the best. Why? Well, Max was only in town to look for Ivy, who was his girlfriend at the time and he was pretending to be Serena’s cousin.
Granted, he did not know all the craziness that Ivy was involved in, but still… Hooking up with him would have come with its fair share of baggage and a troubled ex.
4 Date: Carter Baizen
Carter Baizen was a complex and supporting character on this show. Was he actually nice? Did he just equal trouble? Could he be trusted? The fact that he went through trouble in order to help Serena find her father makes it seem like he was a caring guy.
Plus, he was another cutie, and he came with money and resources; a relationship with him would have probably come with trips to exciting places and dinner dates at fancy restaurants!
3 Disaster: Tripp van der Bilt
Another fling in Serena’s life happened with Tripp van der Bilt; he was Nate’s cousin, he was running for a political office, and he was married, so this was a messy moment.
Yes, Tripp was gorgeous and powerful and kind, but his wife and grandfather were manipulative and untrustworthy. It would have been smart to avoid them at all costs.
2 Date: Steven Spence
In one of the episodes when Serena ran away from her troubles, her friends found her living a new life, with a new name and a new boyfriend: Steven Spence.
The only real flaw that would have come out of dating him would be having to put up with his teenage daughter, Sage. She would grow out of it, though, making it all worthwhile!
1 Disaster: Ben Donovan
Of course, Ben Donovan used to be Serena’s teacher then got sent to prison by Lily. Once he got out, he hung out with/got romantically involved with Serena before moving away.
While he was another attractive, smart, and caring man, he was also related to Juliet. And while they may have forgiven everyone involved with his time behind bars, he is another one on the “disaster” list.
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