Every Gossip Girl Wedding, From Sweet to Scandalous
By Alexus Mosley
There are birthdays, there are debutante balls, and then there are Gossip Girl weddings. Equal parts glamorous and completely unhinged, they gave us breathtaking gowns, unforgettable declarations of love, shocking betrayals, and enough plot twists to keep the Upper East Side buzzing long after the last champagne glass was emptied. So grab your favorite Ladurée macarons…. we’re revisiting every Gossip Girl wedding, from the pilot era to the series finale.
Lily van der Woodsen & Bart Bass
Season 1, Episode 18: “Much ‘I Do’ About Nothing”
The first Gossip Girl wedding was exactly what you’d expect from Manhattan royalty: elegant, extravagant, and hiding more secrets than the Bass family vault. Lily may have married one of New York’s most powerful men, but their union also made Serena and Chuck stepsiblings, creating one of television’s most wonderfully complicated family trees.
Eleanor Waldorf & Cyrus Rose
Season 2, Episode 13: “O Brother, Where Bart Thou?”
While everyone else on the Upper East Side seemed determined to sabotage their own happiness, Eleanor and Cyrus quietly reminded us what a healthy relationship actually looked like. Equal parts heartfelt and hilarious, their wedding officially welcomed the world’s most lovable stepfather into Blair Waldorf’s life—even if she wasn’t exactly thrilled about it at first.
Lily van der Woodsen & Rufus Humphrey
Season 3, Episode 2: “The Freshmen”
After decades of almosts, missed chances, and bad timing, Lily and Rufus finally got their fairy tale. Watching Brooklyn’s favorite former rocker marry the queen of the Upper East Side felt like the show’s ultimate full-circle moment—at least until Gossip Girl reminded us that happily ever after rarely lasts in Manhattan.
Dorota Kishlovsky & Vanya
Season 3, Episode 18: “The Unblairable Lightness of Being”
If anyone deserved a happily ever after, it was Dorota. Her wedding to Vanya delivered one of the sweetest moments in the entire series, complete with Blair proudly stepping into maid-of-honor duties. Amid all the scandals, schemes, and social climbing, this was one celebration that reminded us why we loved the Upper East Side in the first place.
Blair Waldorf & Prince Louis Grimaldi
Season 5, Episode 13: “G.G.”
On paper, Blair’s royal wedding had everything she’d dreamed about since childhood: a prince, a palace, and a gown worthy of Grace Kelly herself. The only problem? Her heart was still somewhere between the altar and Chuck Bass. What should have been a fairy tale became one of the most unforgettable heartbreaks in Gossip Girl history.
Chuck Bass & Blair Waldorf
Season 6, Episode 10: “New York, I Love You XOXO”
Six seasons. Countless breakups. One limo crash. More “three words, eight letters” than we can count. Chuck and Blair’s impromptu Central Park wedding wasn’t the grand society affair anyone expected, but somehow it suited them perfectly. After everything they’d survived together, all Chair really needed was each other.
Serena van der Woodsen & Dan Humphrey
Season 6, Episode 10: “New York, I Love You XOXO”
The boy who spent years watching Serena from afar finally married the girl who inspired his first Gossip Girl post. Their wedding brought the series full circle, reuniting nearly every major character for one last Upper East Side celebration. Love him or hate him, Lonely Boy got exactly the ending he’d been writing all along.