Nikki Glaser Confesses to Gwyneth Paltrow: She Tried to Hook Up with Her Ex Ben Affleck on Raya
Comedian Nikki Glaser dropped a hilarious bombshell on Gwyneth Paltrow’s podcast, admitting she repeatedly swiped right on the actress’s ex-boyfriend Ben Affleck in a failed bid to match on the exclusive dating app Raya. The candid revelation turned into a lighthearted roast, showcasing Glaser’s unfiltered humor and Paltrow’s playful response.
The Podcast Chat: From Golden Globes Jokes to Dating App Disasters
The confession unfolded during the March 24, 2025, episode of Paltrow’s “Goop Podcast,” where Glaser, fresh off hosting the 2025 Golden Globe Awards, discussed her career highs and personal anecdotes. The conversation veered into Glaser’s past experiences on Raya, the celebrity-favored dating app known for its A-list users.
Glaser, 40, recounted how Affleck’s profile kept popping up during her time on the app years ago. “When I used to be on Raya and [Ben] would come across, [I would give him a] very concentrated check mark ‘yes’ and, like, never [got] it back,” she shared, laughing off the rejection. Paltrow, 52, who dated Affleck off-and-on from 1997 to 2000, responded with amusement: “That would have been a good one. He’s gorgeous.”
The exchange tied back to Glaser’s Golden Globes monologue, where she joked about Affleck yelling movie titles “after he orgasms,” adding a cheeky layer to the story. Glaser emphasized it happened “years and years ago,” clarifying she wasn’t currently pursuing him.
Background: Raya’s Celebrity Allure and Glaser’s Dating History
Raya, launched in 2015, is an invite-only app that caters to influencers, actors, and other high-profile figures, maintaining exclusivity with a rigorous vetting process. Glaser, known for her stand-up specials like “Someday You’ll Die” on HBO, has been open about her on-again, off-again relationship with boyfriend Chris Convy since 2013. She’s described their dynamic as a mix of commitment fears and adventure-seeking, even touching on her “hot husband” fetish where she enjoys Convy’s occasional flings with other women—as long as everyone knows the boundaries.
Paltrow and Affleck’s romance in the late ’90s was a Hollywood staple, marked by red-carpet appearances and an engagement that ended amicably. Paltrow has since married producer Brad Falchuk in 2018, while Affleck, recently divorced from Jennifer Lopez, has denied being on Raya despite rumors. In 2023, Paltrow even praised Affleck as “excellent” in bed compared to ex Brad Pitt, keeping their history a topic of intrigue.
Glaser wasn’t done spilling: She also admitted swiping on Andrew Garfield multiple times, saying his profile appeared “so many times” but went unmatched. “I know for a fact he had to have seen my profile… I would have matched with him if he was interested,” she noted, with Paltrow quipping that Garfield “regrets it now.”
Expert Takes and Fan Reactions: Laughter and Relatability
Podcasting experts view the episode as peak entertainment, blending vulnerability with comedy. Relationship coach Esther Perel, in broader discussions on celebrity dating, notes apps like Raya amplify the “fantasy of access” to stars, often leading to humorous mismatches. Glaser’s honesty aligns with her brand of raw stand-up, earning praise from comedy insiders for normalizing rejection stories.
Fans erupted on social media, with X (formerly Twitter) buzzing under hashtags like #NikkiGlaser and #GoopPodcast. One user posted, “Nikki swiping on Ben Affleck and getting ghosted? Iconic rejection story! 😂,” while another joked, “Gwyneth trolling Nikki for wanting her ex is the 2025 energy we need.” The clip went viral, amassing millions of views, as listeners appreciated the no-holds-barred chat on modern dating woes.
Impact on U.S. Audiences: Dating Apps, Hollywood Gossip, and Lifestyle Vibes
For American listeners, this anecdote taps into the cultural obsession with celebrity dating scandals, influencing everything from app usage to pop culture consumption. Economically, it spotlights Raya’s premium model—subscriptions run $9.99 monthly—boosting the $4 billion U.S. dating industry amid post-pandemic swiping surges.
Lifestyle-wise, Glaser’s tales resonate with millennials and Gen Z navigating apps, promoting body positivity and open relationships in a tech-driven era. Politically neutral, it sidesteps controversy but ties into broader tech debates on privacy in exclusive platforms. Sports fans might chuckle at Affleck’s Batman legacy, linking to Glaser’s Golden Globes jabs that poked fun at Hollywood’s elite, including nods to athletes-turned-actors.
Overall, it humanizes stars, showing even A-listers face digital duds, encouraging relatable conversations on rejection and self-growth.
Wrapping Up: A Swipe Right for Honest Hollywood Banter
Nikki Glaser’s bold admission to Gwyneth Paltrow about chasing Ben Affleck on Raya turned a podcast episode into a viral hit, blending laughs with real talk on dating fails. Paltrow’s teasing response highlighted their easy chemistry, proving exes can be fair game for friendly roasts.
As Glaser tours her new special and Paltrow expands Goop’s wellness empire, expect more unfiltered gems. For U.S. fans, this story reminds us that in the swipe-right world, rejection is universal—even for comics eyeing Oscar winners. The future? More celebs spilling on apps, keeping Hollywood’s romantic rollercoaster spinning.