Nikki Glaser met her boyfriend on set in 2013. They've broken up five times since.

If you've ever found yourself wondering if 'on-again, off-again' is a relationship actually going to last, Nikki Glaser has been there. And she's probably made a joke about it to a room full of people.

As the 41-year-old comedian hosts the Golden Globes for the second year running, all eyes aren't just on her savage punchlines, but on the man cheering her on from the wings: her long-term, on-again, off-again boyfriend, Chris Convy.

Their relationship is a decade-long saga that proves love isn't always a straight line — sometimes it's a zigzag that involves five breakups, a height difference and a very specific set of rules regarding "dirty laundry."

Every great chaotic romance needs a meet-cute, and Nikki's happened in the most Hollywood way possible: on set. Back in 2013, Nikki was the star of her MTV talk show Nikki & Sara Live, and Chris was the producer.

Watch: Nikki Glaser Opening Monologue 82nd Annual Golden Globes. Article continues after video.

While Chris was busy making sure the cameras were rolling, Nikki was busy pining. She later described the vibe as a classic The Office scenario.

"I just had a crush from afar, which was so fun because I was just pining for him constantly," she told Graham Bensinger. "It was very Jim and Pam, I was Jim, and he had no idea."

The pair eventually got together, but the professional and personal lines blurred quickly. When her 2016 series Not Safe With Nikki Glaser (which Chris also produced) was cancelled, their relationship followed suit. At the time, Nikki's outlook was peak pragmatism.

"Most relationships don't last, and most TV shows don't last," she told Buffalo News.

Since that first 2013 meeting, the couple has called it quits no fewer than five times, she told Howard Stern in 2024. It's a statistic that might make some of us reach for the weighted blanket, but for Nikki, it's just part of the process.

She's been candid about her fear of "committing to anything forever," once admitting that the idea of "forever" can sometimes feel like admitting defeat. During their "off" periods, she even encouraged Chris to "entertain the idea of being with other women," telling Bensinger she wouldn't mind a fling — as long as it wasn't emotional.

However, the 2020 pandemic changed the game. The pair moved back to their shared hometown of St. Louis to film her reality show Welcome Home Nikki Glaser, a move that forced them to actually, well, deal with each other.

"I had a breakthrough recently where we were kind of maybe going to go our separate ways… and then I just stopped," she told Bill Maher in 2024. "I just realised no one I'm fantasising about replacing him with is going to be perfect. He doesn't need to be perfect for me."

Dating a stand-up comedian is not for the faint of heart, but Chris has a very specific "contract" when it comes to being the butt of the joke.

"He's given me permission," Nikki told People. "He said, 'You can talk about anything on stage about me as long as it's funny. The second it isn't… then we have an issue.'"

Image: Getty

Basically, if the joke kills, the relationship lives. If the joke bombs? The car ride home is going to be silent.

She's used this "hall pass" to joke about everything from their height difference (Nikki is 5'9", Chris is roughly 5'7") to his status as her "hot guy on discount."

In her SNL monologue, she quipped that to get a "10 in the face," you sometimes have to settle for a "5'7" in the height.

Despite the five breakups and the public roasts, the pair seem stronger than ever. Chris was by her side for her historic 2025 Golden Globes debut, and as she returned to host again in 2026.

It's not a fairytale, and it's certainly not traditional, but in a world of curated celebrity romances, there's something refreshing about Nikki and Chris. They aren't pretending it's easy. They're just figuring it out, one joke at a time.

Feature Image: Getty.