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Serena Van der Woodsen's dating history is complicated, to say the very least. Since the dissolution of her relationship with Dan in season one, she dated two former teachers, two con artists, a married politician, three of her friends' exes, and a handful of fairly normal guys relative to Gossip Girl. Like her mother before her, Serena kept a swiftly revolving door of partners, and she liked to mix things up. Ben was Serena's teacher when she was a boarding school student and a minor. The two have feelings for each other, and he's really creepy and inappropriate about it.

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By the time the pair's long-lost secret love child returned from the dead in season three, it really felt like the writers had no idea what to do with them any more. So Lily ended up with William Baldwin, and Rufus ended up with singer-songwriter Lisa Loeb, and nobody lived happily ever after. When you get together in junior high, chances are you're going to grow out of each other before you graduate high school.

Even when Nair Blate?

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Dan was so terrible by the show's end that it was hard to ship him with anyone other than loneliness, but had Vanessa still been around she might have smacked some sense into him. Or at least inspired him to do something better with his time than be Gossip Girl.

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We could have had it all, guys. Remember the very first time Dan and Blair shared a scene, in season one's 'Bad News Blair' aboveand it was unexpected and lovely and a totally authentic moment of connection between two characters you'd never expect to connect? But then Something weird happened. We'll never know exactly what went down in the writers room midway through season five, but Dan transformed from a sweet guy into a sociopath, sabotaging Blair's wedding and isolating her from everyone who wasn't him.

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Eventually the whole relationship was later retconned into an afterthought, with Dan claiming he'd only ever wanted Blair because he was afraid of his love for Serena. Or something.

Top 10 Cutest Gossip Girl Couples

We'd given up caring by this point, and seemingly so had the writers. RIP, Dair. Technically Eleanor and Cyrus should be number one, because they're the only genuinely flaw-free couple in the Gossip Girl universe, but their screen time is a little too limited to bag the top spot. Eleanor was a pretty strong contender for world's worst mother in the first season, but under Cyrus's adorable influence she became warmer and more supportive towards Blair, while Cyrus himself was basically the perfect stepfather.

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These two are proof that real love is possible on the Upper East Side. Oh, Chair. So divisive. So inconsistently written.

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So undeniably hot together. The relationship became, for better or worse, the centre of Gossip Girl for pretty much its entire run, but a couple of seriously questionable storytelling choices in seasons three and four made their epic romance deeply uncomfortable to watch. Clearly realising that they'd gone a little overboard with all the dysfunction, the writers spent the next two seasons trying to rehabilitate Chair.

Apr 26,   Map of Hookups on Gossip Girl Kiss & Tell: Your Official Guide to Gossip Girl's Hookups. April 26, by Entertainment. Shares The kids of Gossip Girl weave quite the tangled web of romantic. It has been almost 7 years as we said goodbye to Gossip Girl, the show with a luxuriant atmosphere and our favorite characters (Serena van der Woodsen, Dan Humphrey, Nate Archibald, Chuck Bass, and Blair Waldorf). So get ready to find out how the lives of the actors of Gossip Girl have changed. Jul 19,   Gossip Girl is coming back to television with a new series of HBO Max! And while the new series won't feature the iconic Serena van der Woodsen or Blair Waldorf, it will definitely be filled with Occupation: Assistant Editor.

So get yourself comfortable and get ready to find out how the lives of the actors of Gossip Girl have changed, for better or worse, since it ended! Who did Leighton Meester date from the cast of Gossip Girl?

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Who married an O. And who dated Zoe Kravitz? While Nate Archibald often swung big on the show, his real-life alter ego Chace Crawford has a far more controlled personality. Chace gained a lot of attention due to his hot Instagram photos and film shoots.

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However, according to Us Weekly, the couple has quietly split up after three years of dating. The actor implied that he was back on the market while discussing his relationship status in an interview with the tabloid.

Throughout 'Gossip Girl,' Serena had her share of great boyfriends, and some really. Oct 16,   Gossip Girl aired from to , causing the world to become entranced with the scandalous lives of Manhattan's elite. The show was considered a bit risque at the time, at least for a teen show, but fans ate it up. If you were a kid or a teen during Gossip Girl's heyday, you probably remember how everyone on MySpace was obsessed with this show and texted each other about it from their. Jun 02,   The Gossip Girl finale has a lot to answer for. It was pretty much a fiasco from beginning to end, but probably the worst sin of all was how it turned Dan .

Following a period as quiet as when Dan was around Serena in the early days of GG, Badgeley has picked up work again in the film Cymbeline. Penn also had a bit of bohemian turn and chose instead to focus on his music career as the lead singer for MOTHXR, while dating fellow actress and singer Zoe Kravitz. These days, Penn is the star of Netflix thriller You and is now married to musician and professional doula Domino Kirke. The couple were romantically linked since their relationship started in but they managed to keep the details of the early days of their romance a secret.

Both actors admit that they weren't very serious at the start of their relationship. Domino said she was never keen to date an actor, having grown up alongside sisters Jemima and Lola, both of whom are actresses. Kirke said the decision to get married was a bit spur-of-the-moment for the couple, catching his bride-to-be completely by surprise.

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The pair actually got married twice. The first time was in Februaryin an intimate ceremony in Brooklyn where Kirke and Badgley officially exchanged vows in front of a small handful of friends and family. The couple then celebrated in June with another, more public event - a bigger reception in upstate New York attended by celebrity guests. Vanessa doesn't change for other people. That's how Jessica Szohr described her character and we cannot agree more!

She also plays a recurring role on Shameless! Szohr recently shared the identity of the man she is dating with her fans.

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She took to Instagram stories to share a snap of her embracing a man. Following the clues, super-sleuth fans uncovered that Jessica is currently dating Arizona Coyotes center Brad Richardson.

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Details from NHL. The couple dated for 3 years until when they broke up, each of the actors only 23 at the time. In an interview with Vanity Fair a couple of years later, Blake revealed that they had had to keep their affair a secret at first as they were afraid the romance could get them into trouble at work:.

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They wanted that because then it fed their whole narrative. People could buy into this world.

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And eventually, that worked. Blake Lively didn't waste any time after the show ended! Not only is she married to Ryan Reynolds and has three baby girls with him, her acting career is heating up too!

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Blake and Ryan celebrated their seventh wedding anniversary on Sept. Blake's name constantly pops up in the news, and her countless hilarious photos on Instagram make us laugh along with her!

Sep 21,   Serena Van der Woodsen's dating history is complicated, to say the very least. Since the dissolution of her relationship with Dan in season one, she dated two former teachers, two con artists, a married politician, three of her friends' exes, and a handful of fairly normal guys (relative to Gossip Girl). RELATED: Gossip Girl: The Main Characters' Family Members, Ranked. Gossip girl dating tree. Chuck finds himself once again at odds with Jack when Chuck learns that his gossip, Elizabeth, is in gossip a con artist in season with Jack and she betrays Chuck by having him sign party the hotel over to Jack. Together, Eleanor Margaret Colin puts Blair in charge of making sure her latest fashion show is a huge. Gossip Girl Wiki is a FANDOM TV Community. View Mobile Site DisneyTrivia EndgameHonest GalaxyQuest.

Blake, like her character Serena, is definitely in the spotlight! There must have been something in the air on the set of Gossip Girl - Jessica Szohr and Ed Westwick were yet another real-life couple to come out of the CW show.

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They began dating more than a year ago after getting to know each other "as friends. But Jessica and Ed broke up after a two-year relationship, shocking fans and leaving them to speculate what really happened between the pair.

Pagesix claimed that Westwick dumped co-star Szohr after hearing rumors she was cozying up with one of his best friends.

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