The Two Iconic Kisses: What Episode Do Dan And Blair Finally Kiss In Gossip Girl?

The question of when Dan Humphrey and Blair Waldorf finally shared their first kiss is one of the most debated and searched topics in the history of the *Gossip Girl* series, even today in December 2025. The truth is, the Upper East Side's most unlikely duo, affectionately known as "Dair," actually shared two major kisses that defined their complex, enemies-to-friends-to-lovers narrative. The first was a tentative, exploratory moment, while the second was the definitive, heart-stopping beginning of their romantic relationship.

For fans looking to pinpoint the exact moment the Lonely Boy and Queen B first locked lips, you need to mark two specific episodes on your rewatch calendar: one in Season 4 and the pivotal, romantic one in Season 5. We break down the context, the consequences, and the full relationship timeline of the most intellectual pairing on the show.

Character Profiles: The Lonely Boy and Queen B

To truly appreciate the significance of the Dan and Blair kiss, one must understand the characters involved. Their pairing was a seismic event that shook the foundations of the Manhattan elite and challenged the show's core love triangles.

• The Unseen Story Jessica Simpsons Battle For Privacy And Body Image In A Digital Age Mlvqa

Blair Waldorf (Played by Leighton Meester)

• Nickname: Queen B, B, Waldorf
• Status: Upper East Side Royalty, Heiress, Fashion Icon
• Family: Eleanor Waldorf (Mother), Harold Waldorf (Father), Cyrus Rose (Step-Father)
• Key Relationships: Chuck Bass (Soulmate/Endgame), Nate Archibald (Ex-Boyfriend), Prince Louis Grimaldi (Ex-Husband)
• Aspirations: Yale, NYU, Columbia, Running Waldorf Designs, Becoming a powerful businesswoman.
• Defining Trait: Scheming, ambitious, a lover of classic cinema and high culture, and deeply loyal to her inner circle.

Dan Humphrey (Played by Penn Badgley)

• Nickname: Lonely Boy, D, Humphrey
• Status: Outsider, Aspiring Writer, Brooklynite
• Family: Rufus Humphrey (Father), Alison Humphrey (Mother), Jenny Humphrey (Sister)
• Key Relationships: Serena van der Woodsen (First Love/Endgame), Vanessa Abrams (Childhood Friend), Blair Waldorf (Romantic Interest)
• Aspirations: Attending NYU, Becoming a published author, Fitting into the Upper East Side world he both loved and resented.
• Defining Trait: Intellectual, moralistic (at times hypocritical), observant, and later revealed to be the anonymous blogger, Gossip Girl.

The First Kiss: A Test, Not a Romance

The very first kiss between Dan and Blair was not the passionate, romantic moment many fans hoped for. Instead, it was a moment of intellectual curiosity and emotional confusion, a direct result of their deepening, yet complicated, friendship.

Season 4, Episode 17: "Empire of the Son"

The initial kiss between Dan and Blair occurs in Season 4, Episode 17, titled "Empire of the Son." This episode aired on April 18, 2011. The context is crucial: Blair is dealing with the fallout of a mysterious "life-changing kiss" she shared with an unknown person, which Chuck Bass has heard about and is determined to uncover.

At this point in the series, Dan and Blair have moved past their mutual disdain and have formed an unlikely, yet powerful, platonic bond. They have become each other's confidantes and intellectual equals, bonding over classic films and shared contempt for the superficiality of their social circle.

• 7 Shocking Things Jessica Capshaw Revealed About Growing Up With Steven Spielberg As Her Stepfather 892ho

The Scene:

• Blair is trying to determine if the "life-changing kiss" was with Chuck.
• Dan suggests that the only way to truly know if a kiss is life-changing is to compare it to one that is decidedly not.
• He proposes that they kiss, arguing that a kiss between them, the two people least likely to ever be romantically involved, would be the perfect control group.
• The kiss happens, and to their surprise—and the audience's delight—it is not the platonic, nothing-burger they expected. Blair is visibly affected, and Dan is left contemplative.

This kiss was the spark that ignited the "Dair" flame, confirming that their connection was more than just friendship, setting the stage for their eventual romantic storyline.

The First Romantic Kiss: The Real Beginning of Dair

While the Season 4 kiss was the first, the true, reciprocal, and romantic kiss—the one that launched the "Dair" relationship—happens much later, after months of emotional entanglement, a royal wedding, and a near-fatal accident.

• The Untouchable Privacy 7 Secrets Of Rachel Mcadams And Jamie Lindens Life Beyond The Red Carpet E820e

Season 5, Episode 15: "Crazy Cupid Love"

The definitive romantic kiss occurs in Season 5, Episode 15, titled "Crazy Cupid Love." This episode aired on February 13, 2012. By this time, Blair has fled her disastrous royal wedding to Prince Louis and is navigating a complex situation with Chuck and her feelings for Dan.

Dan has been Blair's unwavering emotional support through her wedding planning, her near-fatal car crash, and her escape from the Grimaldi family. He has developed deep, undeniable feelings for her, which he has struggled to hide.

The Scene:

• The episode centers around Valentine's Day.
• Blair is trying to figure out what she wants and who she truly loves, still feeling torn between Chuck and Dan.
• After an emotional confrontation where Blair asks Dan what would make him happy, Dan finally stops holding back.
• He confesses his feelings and goes in for a passionate, undeniable kiss.
• Crucially, this time, Blair fully reciprocates. The kiss is a clear, mutual declaration of their romantic feelings for one another, officially transitioning them from friends to a couple.

This moment was a massive turning point for both characters, proving that the intellectual, unlikely bond they shared was strong enough to become a genuine, passionate romance. It cemented the "Dair" relationship as one of the most compelling and controversial plotlines in the series.

The Complete Dan and Blair Relationship Timeline

The journey from enemies to lovers for Dan and Blair was a slow burn, spanning multiple seasons and countless dramatic events. Understanding the full timeline provides context for why those two kisses were so significant.

• Season 1–3: Enemies and Rivals. Dan and Blair are primarily rivals, trading insults and barely tolerating each other due to their opposing social standings and their shared romantic history with Serena and Chuck.
• Season 4 (First Half): Unlikely Acquaintances. They are forced to spend time together, first to help Serena and then out of mutual boredom. They begin to realize they are intellectual equals who share a similar world view.
• Season 4, Episode 14 ("Panic Roommate"): The Friendship Solidifies. Dan and Blair are forced to live together, leading to a deep, genuine friendship based on shared interests and mutual respect. This is the foundation of "Dair."
• Season 4, Episode 17 ("Empire of the Son"): The First Kiss (The Test). The exploratory kiss that confirms their connection is more than platonic.
• Season 5 (Early): Unrequited Feelings. Dan harbors intense feelings for Blair as she prepares to marry Prince Louis. He supports her, even helping her escape her wedding.
• Season 5, Episode 13 ("G.G."): The Royal Wedding Drama. Blair flees her wedding, and Dan is there for her, further solidifying his role as her emotional rock.
• Season 5, Episode 15 ("Crazy Cupid Love"): The First Romantic Kiss. The official start of their romantic relationship.
• Season 5 (Latter Half): The Dair Romance. Dan and Blair officially date, sharing many romantic moments that highlight their intellectual and witty connection.
• Season 6: The Break-Up and The Finale. Their romance ends as Blair realizes her ultimate destiny is with Chuck. Dan is revealed to be Gossip Girl, and he eventually marries Serena, bringing the love square to its final conclusion.

Ultimately, whether you are a "Chair" (Chuck and Blair) or a "Dair" shipper, the moment Dan and Blair first truly kissed—in the romantic sense—remains a highlight of the series, proving that even the most polar opposite characters on the Upper East Side could find love in the most unexpected places.