It seems like every single romantic relationship Dan Humphrey had on Gossip Girl was toxic for one reason or another.

It starts to make you question: Was HE the problem all along?

Here’s a breakdown of why each and every relationship Dan Humphrey had was toxic AF.

Rachel Carr

Dan‘s relationship with Rachel Carr was toxic because she was his high school teacher. He was an underage teenage boy and she was already in her 20s. They had no business hooking up!

Georgina Sparks

Dan’s relationship with Georgina Sparks was toxic because she pretended to be someone else when they first met and later pretended he was the father of her baby even though she knew he wasn’t. Since she was one of the show’s main villains, the fact that Dan dated her at all was bizarre.

Ivy Dickens

Dan’s relationship with Ivy Dickens was toxic because Ivy was completely unstable while they were hooking up. She stopped taking her medication and even asked Dan to call her “Serena” in the heat of a sexual moment. Talk about Weird!

Amanda Lasher

Dan‘s relationship with Amanda Lasher was toxic because she was hired by Chuck to give Dan attention while he was a student at St. Jude’s School for boys. In reality, she was never actually interested in Dan at all.

Willow Weinstein

Dan’s relationship with Willow Weinstein was toxic because she was a little too pushy and aggressive when trying to piece together Dan’s future. Willow got her father involved to further Dan’s career, but she came across as a thirsty try-hard.

Olivia Burke

Dan’s relationship with Olivia Burke was toxic because he was way too insecure to make that relationship last. He knew he was dating a woman out of his league, but he couldn’t get it together or rise to the occasion to be with her.

Vanessa Abrams

Dan’s relationship with Vanessa Abrams was toxic because after their breakup, Vanessa fled to Spain leaving Dan abandoned in New York. Also, Vanessa remained jealous of Serena for pretty much the entirety of her relationship with Dan, which was totally unhealthy.

Blair Waldorf

Dan’s relationship with Blair Waldorf was toxic because she hated him for years and constantly bullied him leading up to their relationship. She was always talking down to him and criticizing him for just about everything from his hair to his hometown.

Serena van der Woodsen

Dan’s relationship with Serena van der Woodsen was toxic because despite the fact that she was his dream girl, he was always posting horrible rumors about her online as Gossip Girl for the entire world to see. What kind of man in love would do something so horrendous?!

None of Dan‘s relationships were as healthy as they should have been. The fact that ended up marrying Serena in the end is still baffling to tons of Gossip Girl fans.

What do you think of Dan’s relationship history? Do you feel like any of his relationships were actually good for him let us know your thoughts in the comment section.