Dan Humphrey

Portrayed as an incredibly talented individual with an interest in poetry, he shares a close bond with his sister, Jenny, evident in his dedication to her schooling and protectiveness of her.

A passionate coffee drinker, Daniel is regarded for his prowess in writing and literature, having previously served as an intern for Strand bookstore during one summer.

Daniel attends St. Jude's Preparatory School for Boys, situated in the Upper East Side, where he interacts with fellow students Chuck Bass and Nate Archibald.

In the initial chapters, he falls in love with Serena Van Der Woodsen after hosting a party at their apartment before heading to boarding school.

Dan explores his sexuality later in the books by starting a relationship with his Strand co-worker, Greg, by making literary salons with him, which were, in actuality, giant orgies.

When he learns from the Gossip Girl site that Serena was seen buying pregnancy tests, he freaks out knowing that the child could very well be his as they've slept together.

Pretending to be "Sarah" and accidentally-on-purpose letting her dog run off its leash in the park, Georgina gets an excuse to talk to Dan.

It is later seen that Dan and Vanessa have taken "Sarah" under their wing as they believe she is a new girl to the Upper East Side who doesn't know her way around.

He eventually gets fired from his summer job due to a lack of commitment and heads to the Hamptons hoping to see Serena.

The reaction to the Dan, Blair, and Serena triangle on "Gossip Girl" polarized viewers and garnered significant media interest.

Meanwhile, Blair, back from her cruise and is currently in Manhattan again, is frustrated with Louis' domineering mother, who feels the need to have complete control over the wedding.

Desperate, Dan turns to Louis for some help, hoping the prince could put some royal weight on it and manage to cancel the publishing.

Soon after, Blair then arrives at Dan's loft and tells him that despite they haven't spoken since the holidays, she needs a friend to talk to and believes that he is the only one that will truly listen.

Blair assumes that he was following her and starts reprimanding him until Dan's conscience gets the better of him and reveals that Louis was only helping him with his book issue.

Once Dan hears Blair throw up, he begins to get worried and, like Beatrice, assumes that she has gone back to her previous bulimic ways.

Soon afterwards, Serena, Nate, Chuck, Louis's mother, Eleanor and Cyrus all know about Blair's pregnancy, and she decides not to keep anymore secrets regarding her unborn child.

Dan monotonously states that she didn't jump on one of the motorcycles and chase Chuck and Blair down the road, but Serena angrily responds that the accident is merely the result of all the amount of damage that Gossip Girl has caused throughout the years.

Dan comforts her and tells her that she should change her mind about marrying Louis, but she insists on pursuing the wedding, stating she's committed to him.

As Blair tells Louis that she's very thankful for giving her a princess title and especially grateful that he gave her another chance, he coldly responds that their wedding was all for show and there is nothing but a contract between them.

Taking her to the airport he realizes just how much she needs to get out of this situation and lies to Serena about her whereabouts, this leaves him with a problem when he is discovered with Blair later on.

In "The Princess Dowry" Dan walks in on Blair discussing what could be a potential way out of her prenup on the phone with Cyrus and another lawyer from his firm.

At CeCe's wake, Chuck outs Dan via Gossip Girl as the sender of the video that was fatal to Blair's marriage.

At first, she thinks that it's just a game Chuck is playing and she is unwilling to participate, however, when she sees the guilty looks on Dan's face she realizes that it's the truth.

Meanwhile, Blair makes a deal with Estee to help her get out of her marriage dowry if there will be no more public mention of it in the media, including Gossip Girl.

Dan cracks a joke that clearly expresses his disbelief and surprise at Blair choosing him over the "love of her life," Chuck.

The new couple make a slow and rocky debut on the Upper East side and are faced with numerous challenges including their relations in the bedroom, Blair's lingering feelings for Chuck, and Serena's distaste for their relationship.

In Season 6, Dan tells Serena that the reason he didn't give her an answer to the "I love you" was because it was easier to focus on his anger at Blair, than to face the possibility of getting what he always wanted in the fear of losing it again.

Dan does not appear in the 2021 sequel series but his Gossip Girl blog is featured in the first episode when Kate Keller find it and decided to relaunch it on Instagram.

[5] Jarett Wieselman of Entertainment Tonight asserted that “charming and disarming in equal measure, Badgley's incarnation of the Brooklyn-boy gone bad was always a comedic and emotional highlight.”[6] Other colleagues have also commented on Dan Humphrey’s character.

"[7] The series executive producer, Stephanie Savage, claimed that “as he [Dan Humphrey] is the outsider, he's somebody who when he's pointing out what's absurd about the world, you have to believe he's smart enough to get it and also deliver it in a way that you find it kind of amusing and not just critical or judgmental.