Gwyneth Paltrow Exposes Nikki Glaser’s Secret Crush On Ben Affleck

Gwyneth Paltrow didn’t hold back when she put Nikki Glaser on the spot during a new episode of her “Goop Podcast,” teasing the comedian for her past interest in none other than Paltrow’s ex,Ben Affleck.

Affleck, who is now single again after divorcing Jennifer Lopez, dated Gwyneth Paltrow off-and-on between 1997 and 2000.

The two dove into Glaser’s history with the celebrity dating app Raya, where she confessed to consistently swiping right on Affleck.

“When I used to be on Raya and he would come across, [I would give him a] very concentrated check mark ‘yes’ and, like, never [got] it back,” Glaser admitted on her podcast.

Paltrow seemed amused and a little surprised at the roster of stars Glaser had encountered while using the app. That includes actor Andrew Garfield, who Glaser says also didn’t return her interest.

“I know for a fact he had to have seen my profile. … I would have matched with him if he was interested,” she said.

Paltrow seemed genuinely excited about the missed opportunity, replying, “That would have been a good one. He’s gorgeous. … Now he regrets it.”

Glaser agreed, adding, “I’m sure he is [interested] now, but why not then?”

The conversation came as the two were reflecting on Glaser’s buzzworthy 2025 Golden Globes monologue, where she poked fun at Affleck’s love life, most memorably with a risqué joke about him yelling out movie titles in the bedroom.

After the awards show, Glaser revealed she had pulled another line from the set. “‘Here’s to Ben Affleck. I can’t wait to see which Jennifer you try to ruin next.’ … That would have been insane,” she said in an interview with Howard Stern.

The joke would have nodded to Affleck’s marriages and subsequent divorces from Jennifer Garner and Jennifer Lopez, both of which followed his early 2000s relationship with Paltrow.

Of course, this isn’t the first time Paltrow has spoken candidly about Affleck.

During a 2023 appearance on “Call Her Daddy,” the Oscar winner didn’t hold back when asked about their intimate past, calling her former “Bounce” co-star “technically excellent” in bed. But when it came time to play a round of “F-ck, Marry, Kill,” she still gave Affleck the axe, opting instead to sleep with Brad Pitt, her former fiancé.

Paltrow also gave Pitt the edge over Affleck in terms of both romance and acting chops, though she did note that Affleck had the better sense of humor.

Meanwhile, Affleck’s presence on Raya has come under scrutiny before.

A user named Nivine Jay made headlines after posting a now-viral clip in which the Oscar-winning actor allegedly sent her a personalized video via Instagram following a missed connection on Raya, the exclusive dating app popular among celebrities. The moment quickly gained traction online, racking up over 3 million views.

“Thinking of the time I matched with Ben Affleck on Raya and thought it was fake so I unmatched him and he sent me a video on Instagram,” Nivine wrote in the video’s caption. She followed it with the footage of Affleck himself, looking directly into the camera and saying, “Nivine, why did you unmatch me? It’s me.”

Plus, back in October 2019, reports surfaced that the "Justice League" star was exploring the dating app scene in search of something serious.

“He seems to want a real partner and is not looking to date a celebrity. He is private and is in a good space right now,” a source revealed at the time. “He has his kids and is focusing on work, but is ready to be in love again.”

Despite those reports, Affleck later pushed back against dating app speculation.

In an interview with Diane Sawyer on "Good Morning America," he denied using any dating “websites,” including mainstream platforms like Tinder, Bumble, and Grindr. “I know people who are on them and they have a fun time, but not me. I would love to have a relationship that was deeply meaningful and one to which I could be deeply committed,” he said.