Comedian Nikki Glaser and her boyfriend, Chris Convy, have been off-and-on for a decade.
“I think the off-and-on is [because] I’m just terrified of committing to anything forever,” Glaser said during a May 2024 appearance on the Howard Stern Show. “I think committing to something forever makes me think of no other adventures. It’s just, kind of, admitting defeat. It’s settling.”
According to Glaser, she and Convy have broken up “probably five times in 10 years.”
“Our breaks have gone from maybe two days to one was three years long,” she recalled. “He’s broken up with me. In the beginning of our relationship, I think I wanted a boyfriend so badly, I really misrepresented who I was.”
With Convy’s assistance and support, Glaser has learned to “stop lying” and become a better person. Keep scrolling to revisit their complete relationship timeline:
2013
Glaser and Convy met on the set of her MTV series, Nikki & Sara Live.
“It was my first TV show and he was a producer on the show and he was from St. Louis, where I was from,” Glaser recalled during an October 2022 appearance on In Depth With Graham Bensinger. “I just quit drinking, like, a year before that and I didn’t want to have any relationships with people who were heavy drinkers.”
According to Glaser, she initially thought Convy was cute but “too fun.”
“It was, like, a party that we all met each other at,” she added. “He was dancing and he was just, like, too fun and smiley. I was like, ‘That guy’s wasted because how could you be that way?’ So, I just wrote him off, like, ‘No not for me.’”
When Glaser realized Convy was also sober, she developed a “crush.”
“I just had a crush from afar for a really long time, which was so fun because I was just, like, pining for him constantly,” she quipped. “It was very Jim and Pam [from The Office.] I was Jim and he had no idea. He was my first real boyfriend.”
Glaser previously told Us Weekly in her 2022 “25 Things You Don’t Know About Me” feature that she had her first boyfriend at the age of 24.
2016
Convy continued to work alongside Glaser, producing her one-season show Not Safe With Nikki Glaser on Comedy Central. Around the same time that the show was canceled after one season, they broke up.
2020
Amid the coronavirus pandemic, Glaser moved back to her native St. Louis and sold her docuseries Welcome Home Nikki Glaser to the E! network. While the TV host initially pitched it as a dating show, she later started seeing Convy again off camera.
“I kinda [wanted] to date someone who will be on camera with me,” she told Graham Bensinger in 2022, then revealing what she told Convy. “I’ll keep seeing you in private, but I have to date on the show unless you want to be on camera and he was like, ‘I’ll do it.’”
Glaser called Convy’s willingness to publicize their relationship a “turning point” because it illustrated how much he loved her.
“He wants to, like, share a thing together, so it was just all these things,” she added. “Then I started doing things that were hard for me to do, like, making time for him.”
2022
During Glaser’s sit-down with Bensinger, she confirmed that she and Convy briefly split that September.
“Last month was like a ‘do-or-die’ situation, where it was like, ‘What are we doing? Where is this leading me?’” she added. “We never talked about marriage. We both signed on nine years ago as people who didn’t want to get married, didn’t want to have kids, but now he’s in his 40s [and] I’m in my late 30s. What are we doing? Our priorities have changed, our goals have changed.”
2024
Glaser offered more insight into their relationship on SiriusXM’s The Howard Stern Show, noting that they previously split over her podcast confessions.
“Not because I thought he won’t hear them, but they would just come out naturally under the guise of ‘it’s comedy!’” she said. “He eventually heard them and goes, ‘I don’t recognize who this person is.’ … He had every reason to break up with me because it was jarring to him because I was just lying all the time. He really got me to stop lying, I’m better at it. I’m not perfect at it because I still fear abandonment, so there’s some issues in our relationship where I fear he’s going to be mad at me.”
June 2025
Glaser discussed the difficulties of deciding to joke about her relationship in her standup acts in an interview with People.
“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, but not really anymore,” she said, adding that Convy is “so cool” and has “given [her] permission” to joke about him.
“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 continued. “‘If you’re just venting up there just to get it off your chest and embarrass me, not good, but if you’re up there and you’re making a solid joke, you can do whatever you want.’”
October 2025
Glaser joked about Convy in her controversial Saturday Night Live monologue, telling the audience, “I do date a short guy.”
“He is shorter than me. But he’s, like, really hot. 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-foot-7] in the height. That’s the trick,” she joked. “It’s like getting a hot guy on discount. He’s marked down. I met my boyfriend at TJ Maxx, clearance rack, he was hiding in it.”
Glaser continued, “It’s crazy ‘cause sometimes I’ll post pictures of us online, and I’ll get comments of, like, ‘Girl, he’s hot.’ Like, ‘How’d you get him?’ And I’m like, ‘If you zoomed out, you’d see he’s sitting on my lap, so this is a tiny guy. Went digging in the bargain bin, ladies.’”
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