comedian Nikki Glaser and her friend, Chris Convyhave been on and off for a decade.

“I think the back and forth is because I’m just afraid of committing to anything forever,” Glaser said during a May 2024 appearance on the Howard Stern Show. “I think when I commit to something forever, I don’t think about other adventures. It’s just a matter of admitting defeat. It calms down.”

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

“Our breaks went from maybe two days to one in three years,” she remembers. “He broke up with me. I think I wanted a boyfriend so badly at the start of our relationship that I really misrepresented myself. I thought getting a boyfriend meant being friendly and just doing whatever, never arguing (and) never saying, “I don’t like what you just said,” because then he would say, “Well, That’s how I am. ‘Bye.'”

With Convy’s help and support, Glaser has learned to “stop lying” and become a better person. Keep scrolling to rewatch the full relationship timeline:

2013

Glaser and Convy met on the set of their 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 In detail with Graham Bensinger. “I just stopped drinking about a year before and didn’t want to be in relationships with people who were heavy drinkers.”

According to Glaser, she initially found Convy cute but “too funny.”

“It was kind of like a party where we all met,” she added. “He was dancing and he was just too funny and smiling. I thought, ‘That guy sucks because how could you be like that?’ So I just wrote him off and said, ‘No, not for me.'”

When Glaser realized that Convy was also sober, she had a “crush.”

“I had a really long-distance crush on him, which was so fun because I was constantly pining for him,” she joked. “It was very Jim and Pam (from The office.) I was Jim and he had no idea. He was my first real friend.”

Glazier previously told Us weekly In her 2022 post “25 Things You Don’t Know About Me,” she reported that she had her first boyfriend when she was 24.

2016

Convy continued to work with Glaser and produced her year-long show Not sure about Nikki Glaser on Comedy Central. Around the same time the show was canceled after one season, they disbanded.

2020

Amid the coronavirus pandemic, Glaser returned to her hometown of St. Louis and sold her documentaries Welcome home Nikki Glaser to the E! Network. While the TV presenter initially pitched the film as a dating show, she later started seeing Convy again behind the camera.

“I kind of wanted to date someone who would be in front of the camera with me,” she said Graham Bensinger in 2022 and then revealed what she told Convy. “I’ll still see you in private, but I have to go out with you on the show unless you want to be on camera and he was like, ‘I’ll do that.'”

Glaser called Convy’s willingness to go public with their relationship a “turning point” because it made it clear how much he loved her.

“He likes to share things with each other, so it was just all of those things,” she added. “Then I started doing things that were difficult for me, like making time for him.”

2022

During Glaser’s meeting with Bensinger, she confirmed that she and Convy had briefly broken up in September.

“Last month it was like a live or die situation: ‘What do we do?’ Where does this take me?’” she added. “We never talked about marriage. We both signed up nine years ago as people who didn’t want to get married and have kids, but now he’s in his 40s (and) I’m in my late 30s. What do we do? Our priorities have changed, our goals have changed.”

2024

On SiriusXM, Glaser offered more insight into their relationship The Howard Stern Shownoting that they were previously divided over their podcast confessions.

“Not because I thought he wouldn’t hear them, but they would just naturally under the guise of ‘This is comedy!’ come out,” she said. “At one point he heard her and said, ‘I don’t know who that person is.’ … He had every reason to break up with me because it bothered him because I was lying all the time. He really made me stop lying, I’m better at it. I’m not perfect at this because I’m still afraid of being abandoned. So there are some issues in our relationship that make me worry that he might be mad at me.”