I don’t think Dan Humphrey and Serena van der Woodsen would have been endgame on Gossip Girl.
The more I watch and rewatch the show, the more settled I become in this belief.
They shouldn’t have been an endgame couple based on how toxic they were together, especially considering the fact that Dan settled with Serena when he really wanted to be with Blair.
Serena ALSO settled with Dan because he was her long-time stalker and cyberbully. I honestly can’t wrap my head around it.
When I go through the list of Dan’s most serious ex-girlfriends on Gossip Girl, I feel that he should have ended up with Olivia Burke instead of Serena. And I have a few reasons why I think so.
And btw, I’m well aware that there are plenty of people who are obsessed with Dan and Serena as a couple, and I know that’s true based on all the lovey-dovey video edits I see of their most romantic scenes.
Gossip Girl fans loved to splice Dan and Serena moments together on YouTube all the time, but I’m personally not a fan of Dan and Serena, and I never was.
I found them boring as a couple. Where was the fire and intensity? Chuck and Blair were so much more interesting to follow. Jenny and Nate were more interesting to follow, too.
Dan and Serena were too toxic to be endgame
The toxicity between Dan and Serena was too insane to deny. It was off-and-on shenanigans, bold-faced lies, Dan falling in love with Serena’s best friend, and Serena ultimately finding out that Dan was her own personal stalker and cyberbully for years? How the hell did they get past that?
I think since everyone expected them to be endgame, the Gossip Girl writers went in that direction anyway, even though they probably shouldn’t have. And Dan really should have just tied the knot with Olivia Burke instead.
And BTW, if Dan and Serena hadn’t ended up together, there’s a huge chance her mom, Lily, and his dad, Rufus, could have been endgame. Fans of Gossip Girl, including myself, were rooting for Lily and Rufus way more than we were rooting for Dan and Serena. I’ve seen a lot of that sentiment in the research I do whenever I’m making Gossip Girl content.
This is partly why I strongly believe Dan should have married Olivia instead of Serena.
They would’ve been public figures together
One of the reasons Dan and Olivia’s relationship failed on Gossip Girl is that he didn’t feel like he could fit into her world easily. He felt like her busy schedule as an actress might’ve been too overwhelming, which is why he pursued his connection with Vanessa instead.
Being with Vanessa was easier for him since their relationship was down-to-earth, normal, and largely out of the spotlight.
But my argument for Dan and Olivia is that he was eventually going to become a public figure himself thanks to the publication of his best-selling novel.
Dan created a level of fame for himself by writing that book, so even if he was never going to be on the same level of fame as Olivia, he would have figured out how to navigate life as a public figure while being married to her anyway.
And it’s an experience the two of them could have shared as a couple.
Olivia could’ve been the person to help him navigate the complexities of fame and notoriety since she was already well-versed in that lifestyle.
This relationship would’ve challenged Dan in the right way
I think Dan should’ve ended up with Olivia as his wife instead of Serena because this is the type of relationship that would have challenged him for the better.
And Dan needed to be challenged when it came to handling his insecurities.
Olivia would have helped Dan thrive in that area. She would have built him up, helped him feel more confident, and been the partner he needed to start viewing himself in a better light with more confidence, self-assurance, and inner security.
He struggled with so many insecurities leading up to his relationship with Olivia because he always felt like he needed to overcompensate since he didn’t feel like he compared to his classmates on the Upper East Side.
Serena wasn’t exactly helpful in challenging him for the better in their relationship.
They had so much random drama scattered throughout their relationship that Dan never had the opportunity to focus on becoming a better version of himself.
With Olivia, I feel like he could have gone through a lot of positive growth and personal development.
I’m not the only Gossip Girl fan who thinks this about Dan, but he was kind of a terrible character in a lot of areas.
He was self-righteous, pretentious, and somewhat of a jerk.
He needed to be lovingly challenged, and Olivia could’ve presented that.
Vanessa would’ve been saved from further heartache
Dan should have married Olivia instead of Serena on Gossip Girl, and this plot change would have saved Vanessa from so much heartbreak on the show.
Whether you hate or love Vanessa, the facts remain the same.
She ended up heartbroken by Dan in a relationship arc that truly never needed to happen.
I have a soft spot for Vanessa because I feel like the Gossip Girl fandom aggressively piles on tons of hatred against her in a way that is a little unnecessary.
I found her annoying in some areas for certain reasons because she was super critical of rich people on the Upper East Side, despite her choice to continually spend time with those very same rich people on the Upper East Side.
But beyond that, Vanessa gets a lot of hatred from the Gossip Girl fandom, and I honestly hate to see it.
I feel like she could have avoided a lot of heartbreak if she hadn’t started dating Dan after his breakup with Olivia.
If Dan and Olivia stayed together and ultimately ended up getting married, Vanessa would have been saved from the heartache of ultimately becoming involved in one of her more toxic relationships on the show.
Vanessa was treated terribly by all the guys she dated on Gossip Girl, and that includes Dan.
Which shouldn’t have been the case since she and Dan had so much history, including years’ worth of childhood friendship behind them.
Yet Dan still struggled to prioritize her in most cases from the very start of her return to Brooklyn.
The final nail in the coffin for Vanessa and Dan was when he found out she sabotaged Serena with the help of Juliet Sharp and his little sister, Jenny.
While he forgave Jenny for her part in that plot, he was never willing to forgive Vanessa.
Vanessa wanted to participate in that plot in the first place because she was constantly being pushed aside by Dan, and it made her feel jealous of Serena.
None of that would have happened if Dan had simply stayed with Olivia the entire time, if you really think about it.
Olivia is the only girl who never hurt Dan
Dan should’ve married Olivia instead of Serena because she’s actually the only girlfriend he dated on Gossip Girl who didn’t hurt him, break his heart, or do something trifling to him.
She’s literally the only rare relationship experience he had that didn’t leave him feeling broken or jaded.
Serena wreaked so much havoc in his life with their super-toxic, off-and-on relationship cycle that came with its own layers of dishonesty and chaos.
Blair Waldorf fully broke his heart when she chose Chuck over him.
Rachel Carr had no business hooking up with him as his high school teacher.
Vanessa broke his trust permanently when she sabotaged Serena.
His fling with Willow Weinstein ended pretty quickly when she overstepped boundaries and tried to make sure Dan would get accepted into a writing program at the Tisch School of the Arts, and she called Dan’s little sister, Jenny, a slur.
Ivy proved herself to be a mentally unstable match for him.
Georgina Sparks proved herself to be a psychotic, blackmailing freakazoid.
And it was revealed that his fling with Amanda Lasher only happened because Chuck Bass paid her to pursue Dan as part of a manipulation plot.
Olivia was really the only girl in Dan’s relationship history who didn’t hurt him.
Ultimately, I feel like Dan and Olivia should have ended up married, and Dan should’ve never tied the knot with Serena.
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