The Unexpected Final Chord: Who Does Rufus Humphrey Really End Up With?

The question of who Rufus Humphrey ends up with has plagued *Gossip Girl* fans since the series finale aired in 2012, and it remains one of the most controversial and debated relationship conclusions in teen drama history. As of December 15, 2025, the official, canonical answer remains a shocking twist that defied years of build-up with his epic love, Lily van der Woodsen.

The former rock star and humble father from Brooklyn ultimately found his final romantic partner in an unexpected, celebrity cameo: the iconic 90s musician, Lisa Loeb. This surprising pairing was briefly shown during the five-year flash-forward in "New York, I Love You XOXO," the final episode of the original series, leaving many viewers wondering why the show’s central star-crossed lovers were kept apart.

Rufus Humphrey: Full Biography and Profile

Rufus Humphrey, portrayed by actor Matthew Settle, is the moral compass and father figure of the *Gossip Girl* universe, at least initially. His journey is one of a Brooklyn outsider trying to navigate the opulent, often corrupt world of the Upper East Side elite. His character arc is defined by his music career, his role as a single father, and his tumultuous, lifelong romance with Lily van der Woodsen.

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• Full Name: Rufus Humphrey
• Portrayed By: Matthew Settle
• Occupation: Former Rock Star (of the band Lincoln Hawk), Art Gallery Owner, Waffle Enthusiast.
• Residence: Started in a loft in Brooklyn, later moved to the Upper East Side with Lily.
• Children: Dan Humphrey and Jenny Humphrey (with first wife, Alison).
• Major Relationships: Alison Humphrey (first wife), Lily van der Woodsen (wife), Ivy Dickens (briefly, controversially), and Lisa Loeb (final partner).
• Key Characteristics: Integrity, passion for music, commitment to his children, and a deep-seated love for Lily.

Rufus’s life was a constant push-and-pull between his grounded, Brooklyn values and the extravagant, manipulative lifestyle of the Van der Woodsen-Bass empire. This internal conflict often manifested in his relationships, particularly with Lily.

The Epic Love Story That Failed: Rufus and Lily van der Woodsen

The relationship between Rufus and Lily van der Woodsen (played by Kelly Rutherford) was the foundational adult romance of the entire series. Their history dated back to the 1980s, a period explored in the spin-off pilot episode, "Valley Girls." They were the ultimate "what if" couple, kept apart by their different social classes and the machinations of Lily's mother, CeCe Rhodes.

They finally married in Season 3, merging their families and creating the iconic blended step-siblings: Dan Humphrey, Jenny Humphrey, Serena van der Woodsen, and Eric van der Woodsen. Their marriage, however, was constantly tested by the pressures of Lily’s past, her wealth, and her ties to the Upper East Side.

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The introduction of Ivy Dickens, a con artist who manipulated her way into the van der Woodsen family, created a major rift. Lily's subsequent choices, including siding with her ex-husband Bart Bass and later reuniting with the duplicitous Dr. William van der Woodsen, ultimately led to the final, irreparable breakdown of her marriage to Rufus.

The tragedy of "Rufly" is that they represented a pure, true love that simply could not survive the toxic environment of the elite New York social scene. Lily chose the comfort, familiarity, and security of her old world (represented by William), while Rufus was left to find a partner who fit his simpler, artistic roots.

The Disappointing End of the Humphrey-van der Woodsen Romance

Many fans were left heartbroken and confused by the final episode’s resolution. The five-year flash-forward showed a happy wedding between Dan and Serena, which logically should have meant their parents, Rufus and Lily, would also be together. However, the show opted for a different path:

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• Lily's Ending: She remarries Dr. William van der Woodsen, Serena’s father, solidifying her place back in the high-society world she was born into. This move was seen by many as a step backward for her character development.
• Rufus's Ending: He is seen at Dan and Serena's wedding reception with a woman who is later identified as musician Lisa Loeb. The scene is brief, showing them together, implying a stable and low-key relationship.

This ending cemented the idea that Rufus and Lily were fundamentally incompatible. Rufus, the former rocker and gallery owner, was happier with a fellow artist who understood his world, while Lily, the socialite, returned to the old-money security of a van der Woodsen.

The Shocking Final Partner: Why Lisa Loeb?

The reveal of Rufus’s final partner, Lisa Loeb, was a classic *Gossip Girl* move—a celebrity cameo and a nod to the characters’ past. Loeb is famous for her 1994 hit "Stay (I Missed You)" and is a real-life musician, which ties directly into Rufus’s background as the lead singer of Lincoln Hawk.

The connection is not entirely random. Lisa Loeb actually appeared in an earlier episode of the series, Season 3, Episode 10, "The Last Days of Disco Stick," where she hosted a VH1 tribute to Lincoln Hawk. This establishes a prior, if brief, acquaintance between the two characters.

The choice of Lisa Loeb serves a distinct narrative purpose:

1. A Return to His Roots: By pairing him with a fellow artist, the show signals that Rufus has finally embraced his true identity as a creative, Brooklyn-based individual, rather than trying to fit into the world of Chuck Bass and Blair Waldorf.
2. Low-Stakes Love: Unlike the constant drama with Lily, a relationship with Lisa Loeb suggests a simpler, more mature, and less complicated life. It's a peaceful ending for a character who endured years of emotional turmoil.
3. A Meta-Commentary: It's a fun, meta-commentary on the show’s own fandom. The creators knew the audience wanted Lily, but they gave Rufus a partner who was a clear intellectual and artistic equal, separate from the UES drama.

Ultimately, Rufus Humphrey ends up with Lisa Loeb, a woman who shares his artistic sensibility and provides the stability he lacked with Lily. While many still mourn the loss of "Rufly," his final relationship suggests a quiet, contented life away from the scandals and secrets that defined his years on the Upper East Side, proving that sometimes, the most peaceful ending is the one you never saw coming.

The Legacy of Rufus Humphrey's Relationships

Rufus’s romantic journey is a microcosm of the show’s themes: the clash between old money and new ambition, and the struggle to maintain integrity in a world of wealth. His relationships with his two wives, Alison Humphrey and Lily van der Woodsen, defined his character for years.

Alison, his first wife and the mother of his children, represented his past life in Brooklyn—a grounded, but ultimately failed, marriage due to her infidelity. Lily represented his aspiration and his great, unfulfilled love, a connection that transcended social barriers but couldn't withstand the pressure of reality.

His brief, ill-advised fling with Ivy Dickens in Season 6 was a low point, a confusing and out-of-character moment that fans often cite as part of his character's "deterioration" after his divorce from Lily. This entanglement, however, served to push him further away from the van der Woodsens and towards a new, healthier path.

The final pairing with Lisa Loeb, while initially jarring, is a symbolic conclusion. It signifies Rufus finally choosing himself and his own world, proving that even in the world of Gossip Girl, a quiet, authentic happiness is possible, even if it’s with a Grammy-nominated musician.