Strange Things About Nikki Glaser's Decade-Long Relationship We Can't Ignore

Comedian Nikki Glaser and her on-and-off again boyfriend, Chris Convy, have been dating for more than 10 years. The two first met back in 2013 on the set of her MTV show "Nikki & Sara Live" where Convy worked as a producer. "I just had a crush from afar which was so fun because I was just pining for him constantly," she said during a 2022 interview on "In Depth with Graham Bensinger." "It was very Jim and Pam, I was Jim, and he had no idea," she added, comparing their meet cute to "The Office." 

Glaser has often talked about the relationship she shares with Convy, even giving him a shout-out — and poking fun at his shorter-than-her stature — during her monologue on "Saturday Night Live" in November 2025. "He's shorter than me. But he's, like, really hot," Glaser joked. "And honestly I think that's why I got him, because I could never get his face on a taller model. Like if you want to get a 10 in the face you gotta go 5'7" in the height," she added. While the two seem very in love, there are undoubtedly some strange things about their relationship that we simply can't ignore.

One of the most interesting — albeit strange — things about Nikki Glaser's relationship with Chris Convy is that they aren't monogamous. In fact, Glaser has been very open about her feelings on her man hooking up with other women. "I'm a weirdo, and I like my boyfriend to at least entertain the idea of being with other women or be with them," Glaser said in her interview with Graham Bensinger. "I think it's about, like, I want to be on HBO Max because I like HBO Max, and it's a cool platform. I want my show to be on a place that is a cool, shiny ... I want things that other people want," she explained. 

When asked if she'd be "cool" with Convy sleeping with someone else, Glaser didn't hesitate. "Yeah," she replied. She went on to compare her take on non-monogamy with her boyfriend eating a meal prepared by someone else. "That's how I look at sex," she told Bensinger, adding, "He likes my cooking the best." Glaser clarified that she's not okay with Convy catching feelings for someone else.

In a 2025 interview on Gwyneth Paltrow's podcast, "goop," Glaser discussed her feelings about non-monogamy a bit more, admitting that Convy had been with other women over the course of their relationship and it didn't bother her — she said it actually turned her on. And while she'd been told her views suggest that she has a "fear of intimacy," she insisted that she feels "so solid" with Convy and doesn't look at it as a fear at all. 

Nikki Glaser and Chris Convy have broken up numerous times over the course of their decade-long romance. There have been various reasons that the two have split and gotten back together, and Glaser previously shared some insight during an interview on "The Howard Stern Show" in May 2024. "I think the off and on is because committing to anything forever, I think that forever makes me think of no other adventures. It's kind of admitting defeat, it's settled," she said. 

Glaser and Convy called off their romance in September 2022 after they questioned where their relationship was headed. They split another time after Convy got upset with Glaser for talking about their personal issues on her podcast. The two were able to work things out, however, and reconciled their issues in that department. "The hardest part is talking about your relationship on stage or injecting jokes where you're upset about something, and you bring it to the stage before you bring it to him. So maybe that's where tension arises," Glaser told People in May 2025.

Nikki Glaser doesn't have the most conventional job and Chris Convy understands that — but he put some ground rules into play as a way to protect some aspects of the couple's private life together. Basically, Convy is okay with Glaser poking fun at their relationship while performing, whether it be during her stand-up set or while she's hosting an award show, but he has drawn a line in the sand. "My boyfriend's so cool," she gushed to People in 2025. "He's given me permission. He said, 'You can talk about anything on stage about me as long as it's funny. The second it isn't, if it bombs, then we have an issue," Glaser explained.

Glaser does poke fun at her relationship and draws on her real life when it comes to her jokes, but she seems to appreciate Convy's take. For example, Glaser took part in "The Roast of Tom Brady" in 2024 and joked about Convy. She called her boyfriend "the love of my life" but said she would "shoot [him] in the ... face" for a chance with the former New England Patriots quarterback. During an interview on "The Rich Eisen Show," Glaser confirmed that she ran the joke by Convy, and he actually encouraged her to keep it in her set.