Nikki Glaser and Chris Convy’s Relationship Timeline

Comedian Nikki Glaser and her boyfriend, Chris Conveybeen on and off for a decade.

“I think the off and on (because) I’m scared of committing to anything forever,” Glaser said during a May 2024 appearance on the 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 settles.”

According to Glaser, she and Convy have have been broken up “probably five times in 10 years.”

“Our breaks have gone from maybe two days to one that was three years long,” he recalled. “He’s broken up with me. At the beginning of our relationship, I think I wanted a boyfriend so badly, I really misrepresented who I was. I thought having a boyfriend meant being happy and doing everything, never fighting (and) never saying, ‘I don’t like what you just said,’ because then he would like, ‘Well, that’s the way I am, bye.'”

With Convy’s help 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 and Sara Live.

“This 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 Detail With Graham Bensinger. “I stopped drinking, like, a year before that and I didn’t want to have any relationship with people who were heavy drinkers.”

According to Glaser, she initially thought Convy was cute but “too much fun.”

“It was, like a party, where we all met each other,” he added. “He was dancing and he was, like, too happy and smiling. I was like, ‘That guy is wasted because how could you be like that?’ So, I just brushed it off, like, ‘No not for me.'”

When Glaser realized Convy sober tooshe developed a “crush.”

“I had a crush from afar for a really long time, which was so much fun because I was, like, pining for it constantly,” she said. “It was very Jim and Pam (oh The Office.) I was Jim and he had no idea. He was my first real love.”

Glaser previously reported Us Weekly in her feature “25 Things You Don’t Know About Me” in 2022 that she had her first love at the age of 24.

2016

Convy continued to work alongside Glaser, producing his show for one season Not Safe With Nikki Glaser on Comedy Central. Around the same time the show was canceled after one season, they broke up.

2020

In the middle of the coronavirus pandemicGlaser moved back to St. Louis, and sold his docuseries Welcome Home Nikki Glaser to the E! network. Although the TV host initially presented it as a dating show, he later started seeing Convy again off camera.

“I wanted to date someone who will be on camera with me,” she said Graham Bensinger in 2022, revealing what he told Convy. “I’ll still see you privately, but I have to date on the show unless you want to be on camera and he was like, ‘I’ll do it.'”

Glaser said Convy’s willingness to publicize their relationship was a “turning point” because it showed how much he loved her.

“He wants to, like, share something together, so it was just all these things,” she added. “Then I started doing things that were difficult for me to do, like making time for him.”

2022

During Glaser’s sit-down with Bensinger, she confirmed that she and Convy had briefly separated that September.

“The last month was like a do-or-die situation, where it was like, ‘What are we doing? Where is this leading me?’” he added. “We never talked about marriage. We both signed up 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 her relationship with SiriusXM The Howard Stern Shownoting that they used to share over her podcast confessions.

“Not because I think he won’t hear them, but they would naturally come out under the guise of ‘it’s comedy!'” he said. “Eventually he heard them and said, ‘I don’t know who this person is.’ … He had every reason to break up with me because it was jarring for him because I lied all the time. He got me to stop lying, I’m better at it. I’m not perfect at it because I’m still afraid of being left, so there are some issues in our relationship where I’m afraid he’ll be mad at me.”