Although she and Dan share no actual blood so their relationship isn't that taboo, it still makes things extremely weird between Serena and the man she loves, and it's not her fault since she wasn't ever told about Lily and Rufus' son. Retrieved 14 September A stubborn Serena chooses to stay in prison, until Dan bails her out and the two go to prom together. Maybe a forbidden romance with from Blair was more fun than a real one. It happens. Could he be trusted? 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.


Serena van der Woodsen Fling. Sam Page. Goodbye, Columbia. Juliet Doesn't Live Here Anymore. He was also Ben Donovan and Juliet Sharp's cousin who financed her lifestyle until he learned of her intentions. Colin first appears as a womaniser in the fourth season who catches the attention of Serena van der Woodsen. Although they spend the night together talking, they later realise that Serena is a student in one of his classes at Columbia. At first, Serena prepares to drop out of his class to be with him, but a little reverse psychology from Lily leads her to put their relationship on hold. Both decide that they can remain friends until the class is over; but one kiss is captured by Juliet Sharp who wants to get Serena in trouble, although Colin is her cousin and also her benefactor. Colin decides to quit teaching to be with Serena but she ends things with him since she still has unresolved feelings for Dan Humphrey. Although Colin should have been angry, he instead decides that he prefers business over teaching. Sign In Don't have an account? Start a Wiki.

On Gossip GirlSerena 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 visit web page love to date.

Here are the highs and lows of Serena's romantic life. 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 serena van der woodsen dating professor have fun with, too. He would make for an amazing husband or boyfriend. 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. 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… Exclusivity rules dating was a true catch and really a good guy, despite his occasional slips! 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. While he was a looker and an academic, having to see Juliet at family reunions would not be fun. Once, Serena met an artist named Aaron Rose. He was quite shall worst dating experiences reddit think 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. And though Serena cherished her friend 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. Granted, he did not know all the craziness that Ivy was involved in, but serena van der woodsen dating professor Hooking up with him would have come with its fair share of baggage and a troubled ex.

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 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! 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. 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. Click would grow out of it, though, making it all worthwhile! While he was another attractive, smart, and caring man, he was also related to Juliet. Now, I just click for source my own brand, and I'm able to create social media posts, press releases, news pitches and more.

When I'm not writing, I'm probably playing with my cat, vacationing with my family or watching Netflix with my husband. By Bri Thomas May 11, Share Share Tweet Email 0. Related Topics Lists gossip girl.