For six seasons, Gossip Girl was the go-to show about teenage friendships, high-end fashion, and passionate romances. The Upper East Siders could go from friends to enemies and from lovers to strangers in a matter of a few episodes. Their emotions were perpetually running high, which led to them making some mistakes in their love lives. After all, dubious dating decisions make for great TV.
Gossip Girl did an excellent job at serving relationship dysfunction as the norm. Besides Eleanor and Cyrus, there is barely any relationship in the show that would stand the test of time in real life. Blair, Serena, Nate, Dan, and Chuck would all be better off if they thought their dating choices through.
10 Lily & Bart
Lily and Bart as a couple make as little sense as Bart's death and resurrection combined. Lily clearly loved men who are sensitive and emotional (such as Rufus), so deciding to marry Bart was definitely a questionable life choice for her.
He hired a PI to spy on her and her children. Why would Bart go to such lengths for a woman he neither loved nor needed? Lily did some pretty horrible things in the show, but marrying Bart was the worst for her personally.
9 Nate & Vanessa
Because she stood no chance in the fabulous world of the Upper East Siders, fans often felt sorry for Vanessa. But when it became clear she was on a rampage to date almost every single male character on the show, we just wanted her to go away and never come back. When she first started seeing Nate, it made sense: she was smart, responsible, and down-to-earth, which is something Nate appreciated.
Once Catherine Beaton, the woman Nate cheated on Vanessa with, got involved in season 2, their relationship became controversial. Red flags were flying high; Vanessa even meddled in Catherine's marriage and went running to Blair for help.
8 Blair & Louis
Prince Louis Grimaldi is one of the men Blair could have ended up with if she didn't want to be with Chuck. Blair considered herself a princess, so it made complete sense to her to accept a marriage proposal from an actual prince. What makes this decision questionable is the fact that Blair didn't really seem to care about who he was as a person.
To her, he was first and foremost a prince, which kind of devoided him of his humanity. At the wedding, it turned out that he was possessive and antagonistic, so Blair really dodged a bullet there.
7 Serena & Steven
Serena wanted to grow up and become an adult, so she did some mental gymnastics and concluded that if she dates an older man, she will surely come across as more poised and collected. So what if he has a daughter who is almost her age?
What's even worse, it turned out that Steven used to date Lily. How would he not know who Serena was? Did the topic of their families never come up?
6 Rufus & Ivy
Ever so often, the parents' storylines were even better than the teens', but Rufus dating Ivy certainly doesn't classify as one. Rufus should have known better than to date someone who socializes with Dan and his friends.
What's even worse, Rufus thought that Ivy was his niece for quite a while. When he hooked up with her, he was clearly in a very bad mental space. He just broke up with Lily, the love of his life, and just wanted to feel better about himself. People in emotional distress tend to make bad decisions.
5 Vanessa & Dan
Vanessa and Dan's relationship was very one-sided from the beginning: she tried to make him stay, while he avoided commitment.
Vanessa truly cared for Dan. One could argue she was a better match for Lonely Boy than Serena. Dan, too, should have known better than to date a girl who crawled through his window uninvited.
4 Blair & Chuck
Blair and Chuck are often hailed as Gossip Girl's best couple, but even their relationship is a truly contentious issue. Blair chose to date a man who shamelessly assaulted other girls and sleep with other women the second he thought he was single. What Blair did after finding out that Jenny slept with Chuck was one of the worst (and most unrealistic) things she's ever done: she banished the poor girl from New York City.
The show sends a very unhealthy message by romanticizing the bond these two share. They might feel crazy about one another, but their passion is perpetually fuelled by some toxic interpersonal drama.
3 Nate & Jenny
Poor Nate. Either he is trying to save his father from addiction issues or he is swooping in to save Jenny from herself. These two clearly care about one another, but their 'romance' was built around the fact that Jenny's well-being largely depended on Nate being there for her.
Nate clearly struggled to understand the difference between caring for someone and being attracted to someone, as is usually the case with parentified children.
2 Serena & Dan
Dan was obsessed with Serena the second he laid his eyes on her and he would do anything to make her his. To him, she was an object, a prize to be won. Even after Serena found out that he is in fact Gossip Girl, the person who emotionally tortured her for years, she still went ahead and married him.
Serena only dated Dan (and most other men) because she was insecure. She needed someone to validate her to feel better about herself. Whether that's healthy or not is not even up to debate: the answer is a loud and clear 'no'.
1 Blair & Dan
Blair and Dan were both smart, analytical, and ambitious. These two characters would have actually made a lot of sense if it wasn't for all the history in their friend group. After all, they challenged one another and helped each other grow.
A good match or not, dating your best friend's ex is dubious enough as it is, especially if it's clear that the ex never really got over the best friend in the first place.
"gossip" - Google News
January 23, 2021 at 04:30AM
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10 Questionable Dating Choices In Gossip Girl | ScreenRant - Screen Rant
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