TV Romances
All of Dan Humphrey’s Girlfriends on ‘Gossip Girl’, Ranked
Dan Humphrey (Penn Badgley) may have been known as “Lonely Boy” on Gossip Girl, but his long list of love interests throughout the series tell a different story.
Of course, no matter how many women he dated, it always came back to Serena van der Woodsen (Blake Lively). Dan and Serena ended up together at the end of Gossip Girl — yes, even after he dated her best friend — but that doesn’t necessarily mean she was the best choice for him.
So, where exactly does Serena fall in a ranking of Dan Humphrey’s list of girlfriends? After all, he did date some women who turned out to be pretty evil and were in it for the wrong reasons. There may be some controversial takes on this list, but we rounded up a ranking of Dan’s love interests from best to worst. Scroll down to see where all of the women in Lonely Boy’s life landed as we celebrate the return of Badgley’s hit series You.
7. Rachel Carr
A high school student dating their teacher? Sorry, but this was an immediate no. Although Rachel Carr (Laura Breckenridge), Dan’s high school teacher, was sweet and turned to Dan for comfort after Blair’s (Leighton Meester) bullying, this relationship was simply too weird.
6. Ivy Dickens
Sorry, but Ivy (Kaylee DeFer) was the absolute worst. DeFer’s character was actually introduced as Serena’s cousin. Charlie. However, it turned out that Ivy was just an actress who was hired by Serena’s aunt, Carol Rhodes (Sheila Kelly), to impersonate Charlie in hopes of gaining access to her trust fund. Everything Ivy did was based on a lie … including the way she manipulated Dan into dating her.
Of course, her scheme all fell apart when she dressed just like Serena and asked Dan to call her Serena during an intimate moment. A true trainwreck.
5. Blair Waldorf
I know there are a lot of Dair fans out there, but this simply didn’t work for me. Yes, it briefly resulted in a fun enemies-to-lovers storyline when Dan and Blair got together, but it was clear that they were not meant to be. Blair was always meant to be with Chuck (Ed Westwick), point blank, so this one just didn’t feel believable.
But I support all the Dair fans and I hear you!
4. Georgina Sparks
Okay, I know Georgina Sparks (Michelle Trachtenberg) was totally evil, and her pretending that Dan was the father of her child was completely unhinged. But Georgina was the best kind of TV villain. She kept things interesting and she made sure everyone on the Upper East Side was always on their toes.
Georgina and Dan didn’t belong together, but it was a fun fling. Plus, they have the connection of both being Gossip Girl (Georgina briefly ran the site after the real GG – Dan – abandoned it in Season 5).
3. Serena van der Woodsen
I know Serena was Dan’s endgame, but I still don’t think they were the perfect match. The “rich-girl-falls-for-poor-boy” thing was fun in the beginning, but as the series went on, it became clear that Serena and Dan just weren’t each other’s one true love.
Sorry, but Dan deserved better. Even though he was exposed as Gossip Girl, it didn’t ever really seem like he had malicious intentions. Serena tried to pretend she was a better person than the other rich Upper East Siders, but deep down, that’s who she was to her core. Being with Dan was never going to change that.
2. Olivia Burke
Dan’s relationship with Olivia (Hilary Duff) seemed the most real out of all of his romances. He met her at NYU and had no idea she was actually a famous actress, which was so Dan Humphrey-coded. Although they faced some obstacles once Dan discovered Olivia’s identity and their relationship was exposed to the public, they worked well together.
Olivia was a good person. If only she and Dan hadn’t decided to engage in a threesome with Vanessa (Jessica Szohr), maybe this could have worked out. Somehow, despite being a celebrity, Olivia was the most down-to-earth of Dan’s girlfriends. I kind of loved them together!
1. Vanessa Abrams
Szohr leaving Gossip Girl at the end of Season 4 kind of derailed any possibility of Dan and Vanessa ever ending up together, but I still think she’s the person he probably belonged with. Since they knew each other their whole lives, she understood him on a level that nobody else did. She knew more about him than anybody else did. And after their threesome with Olivia, Dan finally realized his feelings for Vanessa were more than platonic.
Yes, it’s a weird way to start off a relationship after years of friendship (and a brief teenage romance in the past), but whatever it takes, right? They eventually became friends with benefits before fully diving into a relationship again.
Although things ended when Dan was caught sleeping in bed with Serena while Vanessa was away, and then she returned to the (fake) news that he had fathered Georgina’s child, Vanessa still always stood by Dan. Even when she was betraying him – like when she stole and sold the book he did not want published because it exposed his family and friends – she did believe it was because it was what was best for him.
Every Gossip Girl character is a little bit evil. Yes, Vanessa had her flaws, but of all of Dan’s love interests, she was the best match for him.
