Gossip Girl brought the drama, meaning there were always catfights, familial issues, popularity battles, and love life problems featured on this teen drama TV show. And while every relationship comes with its fair share of challenges, the main characters in this story made some really big mistakes over the years.
Not following girl code, not honoring marriages, not thinking before acting…yes, each star of this series hit some bumps in the road, when it came to the romance department. It made for exciting television, and it surely taught fans some lessons, such as don’t follow the leads of those on Gossip Girl!
Serena Hooked Up With Her Bestie’s Boyfriend
At the beginning of the show, two best friends, Serena and Blair, weren’t in a good place. Why? Blair found out that Serena hooked up with Blair’s long-time boyfriend, Nate.
The members of the core group were all pals and had been for some time, and later on, Nate and Serena did end up dating. However, they could have and should have waited until they were both single before deciding to get involved with one another.
Nate Cheated On His GF With Her BFF
This was a two-person mistake, though, as Serena betrayed her bestie, and Nate cheated on his girlfriend. Nate and Blair were the power couple, both from well-off families, both gorgeous and both planning for their future.
However, no one can resist the blonde it girl that is S. Still, Nate needed to keep it in his pants, make up his mind and not think he could have his cake and eat it, too.
Blair Slept With The Love Of Her Life’s Uncle
Blair wasn’t innocent either, and one of her biggest slip-ups involved Jack Bass. Jack wanted to steal The Empire, and during that time, he blackmailed Blair, saying that she could save it if she slept with him.
Oh, sleep with him again…. yes, she had slept with him before and made him promise not to tell anyone, especially Chuck since she was in love with him.
Chuck Chose A Hotel Over The Love Of His Life
In a crazy twist, Jack revealed that Chuck knew about the hotel drama and deal; he was going to sell Blair out, all in order to protect his hotel. This led to one of several breakups between Chair.
Blair was just trying to help Chuck, and Chuck just was trying to create the best life for them. However, both of their decisions backfired in a nasty way.
Dan Got Involved With A Teacher (Rachel Carr)
Since Dan and Jenny Humphrey weren’t technically from the Upper East Side, they started out as the good kids on the show. That changed. A relationship mistake Dan made was getting involved with a teacher.
Sure, she was cute and interested in things that he liked and great to talk to, but it was a teacher. However, the blame wasn't solely on Dan. Rachel had just as much blame and should've known better than get involved with Dan.
Jenny Got Involved With A Drug Dealer
And Jenny got involved with a drug dealer. She met Damien Dalgaard during her rebellious stage, and they started doing business together and dating.
First, he, well, was part of some not-so-great stuff. Next, he pressured her physically, which led to a breakup. Then, one of Damien's clients called Little J out for being a drug dealer… right in front of Rufus. Wanting to hang out with this guy at all in the first place was not a good move on her part.
Vanessa Ruined All Of Her Relationships With One Huge Mistake
Back in the day, Vanessa Abrams and Dan were really good friends, and they even ended up dating. Vanessa also sort of became friends with this core group and even was romantically involved with a couple of other guys in the group.
But then she partnered up with Jenny and Juliet, in order to take Serena down, and that one move ruined all of her relationships. She was kicked out as a friend and certainly as anything more, and she ended up moving away.
Blair Faked It
Another time Blair messed up was when she faked it. See, she had been with Nate for quite some time, but then the limo scene happened, and she lost her virginity to Chuck. Later, when she and Nate finally decided to take the next step, she faked her virginity for him!
Of course, this news got out, and no one was happy with her.
Serena Had An Affair With A Married Man
Once, Serena had an affair with a married man: Tripp van der Bilt. He was Nate’s cousin, he was running for office, and he was wed to Maureen. Yet this girl who could have anything and always got what she wanted could not help herself.
Nate Had An Affair With A Married Woman
Similarly, Nate had an affair with a married woman. Her name was Catherine Beaton, and while it made for a spicy summer, it was a very complicated situation.
She was married to Lord Beaton, and her stepson was Marcus Beaton. Marcus was dating Blair, yet he and Catherine were also hooking up!