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The Definitive Dair Timeline: When Do Dan And Blair Date In Gossip Girl?

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For fans still debating the ultimate endgame of Gossip Girl, the brief but intense romance between Dan Humphrey and Blair Waldorf—affectionately known as "Dair"—remains one of the most compelling and contentious storylines in the show's history. As of December 21, 2025, the definitive answer to the question of when Dan and Blair date is firmly rooted in the latter half of Season 5, a period that saw the ultimate Upper East Side Queen B find an unexpected intellectual and emotional equal in Brooklyn’s "Lonely Boy." Their official dating period, though short-lived, was a pivotal moment that redefined both characters and challenged the established dynamics of the series.

The relationship between the two main frenemies evolved from bitter rivals to unlikely friends, and finally, to a passionate couple, spanning roughly from Season 4 into the final episodes of Season 5. This article breaks down the exact timeline, the reasons the pairing resonated with so many viewers, and the ultimate plot forces that brought their unique romance to an abrupt end.

The Definitive Dan and Blair Dating Timeline (Season 4 to Season 5)

The journey from "I hate you" to "I love you" for Dan and Blair was a slow burn, built on shared contempt for the frivolousness of the Upper East Side elite and a mutual love for high culture, classic films, and witty banter. Their romantic arc can be broken down into three distinct phases:

Phase 1: The Intellectual Friendship and First Kiss (Season 4)

The foundation of Dair was laid in Season 4, following Blair's tumultuous breakup with Chuck Bass and Dan's continued on-again, off-again relationship with Serena van der Woodsen. They begin to lean on each other for schemes, comfort, and intellectual conversation, realizing they are the only two people who truly "get" the other's ambition and cynicism.

  • Key Episode: "The Kids Stay in the Picture" (Season 4, Episode 16): This episode solidifies their bond as they work together on a scheme, leading to a moment of genuine connection.
  • The First Kiss: "Empire of the Son" (Season 4, Episode 17): In a moment of high emotional confusion and stress, Dan and Blair share their first kiss. This kiss, while initially a source of denial and awkwardness, irrevocably shifts their dynamic from platonic friendship to romantic possibility.

Despite the kiss, they retreat back to friendship for the remainder of Season 4, with Blair pursuing her royal aspirations with Prince Louis Grimaldi.

Phase 2: The Official Romance (Season 5, Episodes 17–24)

The "Dair" relationship officially begins in Season 5, following Blair's disastrous wedding to Prince Louis Grimaldi and her subsequent escape. Trapped in a restrictive marriage and a prenuptial agreement, Blair finds solace and genuine affection with Dan, who steps up as her protector and confidant.

  • Official Start: "The Princess Dowry" (Season 5, Episode 17): This is the episode where Dan and Blair officially begin dating. After a series of secret meetings and shared moments, they acknowledge their feelings and step into a romantic relationship, much to the shock of their friends and the entire Upper East Side.
  • The Honeymoon Period (S5E18 - S5E23): For the next several episodes, Dan and Blair enjoy a surprisingly functional and healthy relationship. They support each other's careers (Blair's work at *W* Magazine and Dan's writing), attend events together, and share a deep, mutual respect that many argued was missing from Blair's relationship with Chuck.
  • Episode Highlight: "The Fugitives" (Season 5, Episode 21): Dan sacrifices his chance to go to Rome to be with Blair, demonstrating his commitment.

Phase 3: The Abrupt End (Season 5 Finale)

Despite the logic and maturity of their pairing, the relationship was ultimately a bridge for Blair to realize her true feelings for her long-time love, Chuck Bass. The dating period was short, lasting approximately 7-8 episodes of the season.

  • The Breakup: "The Return of the Ring" (Season 5, Episode 24): In the Season 5 finale, Blair is forced to choose between Dan and Chuck. She realizes she is still deeply in love with Chuck, telling Dan that while she loves him, she is not *in* love with him. The episode ends with Blair choosing to pursue Chuck, effectively ending her romantic relationship with Dan.

Why 'Dair' Worked: The Unexpected Intellectual Connection

The "Dair" pairing was a massive hit with a significant portion of the fanbase because it presented a different kind of love story, one based on intellectual compatibility rather than dramatic, co-dependent passion. Dan Humphrey, the aspiring writer and outsider, saw past Blair Waldorf's "Queen B" facade, recognizing the intelligent, ambitious, and vulnerable woman beneath the headbands and schemes.

Their relationship was characterized by:

  • Mutual Respect: Unlike Chuck, Dan never treated Blair as property or a game. He encouraged her ambition and celebrated her intelligence.
  • Shared Interests: They bonded over classic literature, foreign films, and a cynical view of the Manhattan elite, a connection neither of them shared with their respective primary love interests, Serena and Chuck.
  • The "Healthier" Dynamic: Many fans and critics pointed out that Dair was a much healthier relationship than the highly toxic, yet iconic, "Chair" pairing. Dan and Blair helped each other grow, while Chuck and Blair often indulged each other's worst impulses.

The pairing’s success was a testament to the chemistry between actors Penn Badgley (Dan) and Leighton Meester (Blair). In fact, Penn Badgley himself has voiced his opinion that Dan and Blair should have ended up together, adding a layer of behind-the-scenes support for the pairing.

The Real Reason Dan and Blair Broke Up (The Writers' Choice)

Despite their strong connection and the compelling narrative of their intellectual romance, Dan and Blair’s relationship was ultimately a casualty of the show's established narrative trajectory. The writers had always positioned Chuck Bass and Blair Waldorf as the central, dramatic, and often dysfunctional "endgame" couple, and Dair was seen by many as a narrative detour.

Many retrospective analyses and fan discussions suggest that the relationship was introduced too late in the series and served primarily as a plot device. Specifically, Dan’s role as Blair's boyfriend was essential for her to:

  1. Escape Prince Louis: Dan provided the emotional and logistical support Blair needed to get out of her royal marriage contract.
  2. Settle Her Feelings: The relationship with Dan forced Blair to confront the difference between a love that is comfortable and supportive versus the fiery, all-consuming passion she had for Chuck.
  3. The Chuck Bass Obstacle: The writers needed a final hurdle for Chuck and Blair to overcome, and Dan served as the perfect, yet temporary, rival for Blair's heart.

It is also worth noting a key difference between the show and its source material: Dan Humphrey and Blair Waldorf do not share a friendship or romantic relationship in the original *Gossip Girl* novels. Their unexpected chemistry and storyline were entirely unique to the television adaptation, making the writers' decision to ultimately break them up even more controversial for the dedicated "Dair" fanbase.

By the time Season 6 begins, Dan and Blair are no longer friends, let alone lovers, and Dan's subsequent actions—including his controversial final reveal as the true Gossip Girl and his publishing of the tell-all book *Inside*—further solidified the end of their special bond, though they do reconcile in the five-year flash-forward.

The Definitive Dair Timeline: When Do Dan and Blair Date in Gossip Girl?
when do dan and blair date
when do dan and blair date

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