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Spoilers for the original CW series, including its finale. Dan Humphrey’s best love interest depends on what “best” means: Vanessa offers the deepest shared history, while Serena is his defining romance and the person he eventually marries. This subjective ranking weighs emotional understanding, honesty, relationship health, on-screen development, and story significance—not just endgame status.
How this ranking works
This list covers Dan’s romantic interests in the original Gossip Girl television series (2007–2012), not the books or the 2021 sequel. The show’s romantic stories are full of secrets and betrayals, so narrative importance is not the same thing as a healthy match. The order below reflects a balance of how well each pair understands one another, what their relationship is actually like on screen, and how much it matters to Dan’s story.
| # | Preview | Product | Price | |
|---|---|---|---|---|
| 1 |
|
Gossip Girl: The Complete Series (Repackaged/DVD) | $46.20 | Buy on Amazon |
| 2 |
|
Gossip Girl:S1 (DVD) | $9.25 | Buy on Amazon |
Dan Humphrey’s love interests, ranked
1. Vanessa Abrams: the strongest shared history
Vanessa is Dan’s longtime friend, giving their relationship a level of familiarity that few of his romances can match. Executive producer Josh Schwartz described the shift from friendship to romance: “They’ve been friends for so long. She had feelings for him awhile ago and then he discovers he has feelings for her.” Schwartz told TV Guide that the relationship grew from that history.
That foundation makes Vanessa a compelling choice for best understanding, but it does not make the romance secure. Their relationship ends after Dan cheats on Vanessa with Serena while Vanessa is away. Vanessa ranks first here for familiarity and connection, with the betrayal as a significant mark against the relationship.
#1 Best Overall
2. Serena van der Woodsen: the defining romance and endgame
Serena is central to Dan’s romantic story from the start. The CW’s original overview introduces Dan as dating “the girl of his dreams” after a chance encounter, with Vanessa’s return complicating the relationship. The CW’s series overview captures that early triangle. ITVX’s episode guide follows Dan planning their first official date and later describes the pair acknowledging that they are “crazy about each other.” ITVX’s episode guide traces the early relationship.
Serena and Dan repeatedly break up, and their secrets and class differences make their compatibility debatable. Their importance to the series is not: they resume dating in season six, and the finale’s five-year flash-forward shows them married. TV Insider’s finale recap recounts that ending. Serena ranks below Vanessa only because this list gives shared understanding and relationship experience weight alongside endgame status.
3. Olivia Burke: a promising, relatively grounded short romance
Dan meets Olivia, a Hollywood actor, at NYU. Compared with his more tangled relationships, their romance can feel comparatively grounded, though Olivia’s fame and the threesome storyline complicate it. That “real-feeling” description is one critic’s assessment, not a measure of audience consensus. Schwartz described the Dan–Vanessa–Olivia storyline as tentative and said it had emotional repercussions for the characters. His TV Guide interview offers a creator’s perspective on that triangle.
4. Blair Waldorf: real chemistry, difficult partnership
Dan and Blair move from antagonism and friendship into a romance that develops in ways neither might have expected. Executive producer Joshua Safran said the writers came to see “something real there between Dan and Blair” as their relationship deepened. Safran discussed the pairing with TV Guide, while also describing the challenge of making them work as a couple.
The relationship is a serious contender if character development and intellectual connection matter most. It ranks below the first three because its promise does not make the partnership easy, and Dan ultimately ends up with Serena.
5. Georgina Sparks: entertaining chaos, not stability
Georgina brings mischief and comic unpredictability, making the pairing lively to watch. But the relationship is better understood as a fling than a sound long-term match, especially given Georgina’s false claim that Dan fathered her child. Enjoyable drama is not the same as trust or compatibility.
Rank #2
6. Ivy Dickens: too much deception for a solid match
Ivy’s relationship with Dan takes place amid her impersonation of Serena’s cousin Charlie. That deception undermines the trust a romance needs, leaving little room to treat the pairing as a healthy match.
7. Rachel Carr: an inappropriate power imbalance
Rachel is Dan’s high-school teacher. The teacher–student power imbalance is the decisive issue here; it is not a playful obstacle or a relationship to endorse as an equal partnership.
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Who was Dan’s best girlfriend?
There is no objective or measured fan-consensus ranking. A 2025 TV Insider/Swooon list offers a different subjective order: Vanessa, Olivia, Serena, Georgina, Blair, Ivy, then Rachel. The difference illustrates how rankings change with the criteria: placing greater weight on endgame favors Serena, while valuing shared history favors Vanessa. That ranking and its finale recap are available from TV Insider; they are editorial opinion, not poll results.
Who does Dan end up with?
Dan ends the original series married to Serena in the five-year flash-forward. That makes Serena his endgame partner and defining relationship, but it does not settle every question about who understood him best or which romance was healthiest.
Sources and scope
The CW’s series overview establishes the initial Dan–Serena–Vanessa setup, while ITVX supplies episode-level summaries of their early story. Producer interviews with Josh Schwartz and Joshua Safran document creative perspectives on the Vanessa, Olivia, and Blair relationships; those views are not neutral verdicts on relationship health. Netflix Tudum described the original series as six seasons and reported on October 29, 2024, that all six were streaming on Netflix in the US at that time. Netflix Tudum’s series overview is dated, and streaming availability can change.
Quick Recap
Product prices and availability are accurate as of the date/time indicated and are subject to change. Any price and availability information displayed on Amazon at the time of purchase will apply.
