Leonardo DiCaprio’s long running reputation for dating younger women became the punchline of the night at the 2026 Golden Globe Awards, and his face showed just how tired he might be of the joke. During her opening monologue, host Nikki Glaser zeroed in on the actor’s current relationship and history, drawing a visible, if restrained, reaction from the star as cameras cut to his table. The moment instantly became one of the ceremony’s defining clips, crystallizing the tension between awards show roast culture and a celebrity who has heard the same gag for years.
Glaser’s material landed with the room, but DiCaprio’s tight smile and shifting expression suggested discomfort rather than delight. As the bit unfolded, the crowd laughed and applauded while he appeared to force a grin, glancing away as the camera lingered. The exchange underscored how a familiar late night punchline can feel very different when it is delivered directly to its subject in front of the industry and a global audience.
Nikki Glaser’s sharp monologue and the DiCaprio punchline
Nikki Glaser arrived at the Golden Globe Awards with a clear mandate to keep the show moving and the jokes sharp, and she did not hesitate to lean into the room’s biggest targets. Earlier in the night, coverage highlighted how Golden Globe Awards organizers trusted her to host solo, and she used that freedom to take aim at everyone from studio bosses to streaming platforms. She also worked in topical material about the Epstein files and the state of the industry, setting an irreverent tone before she pivoted to DiCaprio. The structure of the monologue made the eventual jab feel inevitable, building from broad institutional targets to one of Hollywood’s most recognizable faces.
When she finally turned to Leonardo, Glaser framed the joke as “low hanging fruit” that she had tried to avoid, then went ahead anyway. Reports describe her praising his “countless iconic performances” and the fact that he has worked with every great director, won three Golden Globes and an Oscar before undercutting the tribute by saying audiences still mostly talk about his girlfriends. She then zeroed in on his current partner, noting that DiCaprio is dating 27 year old model Vittoria Ceretti, and cracked that “we don’t know anything else about you, man,” a line echoed in multiple recaps of the night.
How DiCaprio reacted in the room
The camera cut to DiCaprio as Glaser delivered the punchline, and his body language told its own story. Clips shared from the broadcast show him sitting at his table as the host joked that his love life is the only thing people discuss, with his expression tightening into what looked like a strained smile. One widely circulated segment, flagged in a Watch clip, captures him shifting slightly in his seat as the audience roars, a small reaction that reads as discomfort when slowed down and replayed online.
Observers noted that Glaser, who is 41, seemed aware of the awkwardness she had created and quickly went meta on her own material. She followed up by apologizing to “Leo,” saying “I’m sorry I made that joke, it’s cheap, I tried not to,” a line that appears in both See the recap and other coverage. Another account quotes her adding that she knew “you’ve worked with every great director” but that people still fixate on his girlfriends, reinforcing the idea that the gag was as much about Hollywood’s obsession with his dating life as it was about DiCaprio himself.
The long running joke about younger girlfriends
Glaser’s decision to go there did not come out of nowhere, it tapped into a long running pop culture narrative about DiCaprio’s relationships. Over the years, his pattern of dating women in their twenties has been dissected in memes and late night bits, and Glaser leaned into that history by saying she had “tried not to” make the joke but could not resist. One report notes that Nikki Glaser went for the “low hanging fruit” of his much younger girlfriends, while another recounts her line that “we don’t know anything else about you, man,” which appears in a Jan write up of the monologue. The repetition of that phrase across outlets shows how quickly it became the shorthand for the entire exchange.
Glaser’s own framing acknowledged that the bit was hardly original. In a segment highlighted under a NEED and KNOW style breakdown, she called the joke “cheap” even as she delivered it, essentially preempting criticism that she was recycling an old punchline. Another recap of the Golden Globe Awards monologue notes that she made clear she was aware of the cliché, which may explain why DiCaprio’s reaction looked more resigned than outraged.
A host who spread the hits around
Part of what made the DiCaprio moment stand out is that it came amid a barrage of jokes aimed at powerful institutions and other stars, not just one actor’s personal life. Glaser used her platform to needle CBS, calling it the “newest place to see BS news” as she riffed on the network’s restructured news division and recent coverage of the Epstein files. She also took gentler swings at Julia Roberts, a contrast noted in a piece that described how Nikki Glaser went “gentle on Julia” while being far more pointed with “Leo.” That contrast heightened the sense that DiCaprio, in particular, was being put on the spot.
Another account of the night underscores how Glaser’s monologue moved briskly from topic to topic, from the One Battle After star to the broader state of awards shows. A live blog of the Live Updates highlighted how the room responded to her blend of industry in jokes and headline driven material, with the DiCaprio gag singled out as one of the biggest reactions. In that context, his apparent unease reads less like a personal feud and more like the cost of doing business at a show that has increasingly embraced the roast format.
Backstage context and the night around the joke
While the monologue dominated social media, DiCaprio’s night at the Globes included other small moments that fed into the narrative. One report describes how security briefly stopped Leonardo from heading to his seat during Snoop Dogg’s bit, with a reporter named Chase noting the interaction on social media. That anecdote, combined with the on camera reaction to Glaser’s joke, painted a picture of an evening where the actor could not quite move through the ballroom unnoticed.
Glaser, for her part, seemed intent on making sure the audience understood she was in on the joke about her own material. In another recap, the writer notes how She doubled back to apologize to “Leo” and joked about turning the controversy into a “sexy leather handbag,” a line that underlined her self awareness. Another piece on the same exchange emphasizes how Leonardo was dragged into the bit alongside other hot button topics, reinforcing that he was one target among many. Still, the image of his uncomfortable smile as Glaser joked about his girlfriend is likely to be the moment that lingers longest from this year’s show.
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