We Can't Ignore The Red Flags In Nikki Glaser's Relationship With Boyfriend Chris Convy

In the world of comedy, Nikki Glaser is a force to be reckoned with. From hosting the Golden Globes two years in a row to launching "The Nikki Glaser Podcast," the stand-up comedian has left her mark on the industry, and we don't see her retiring anytime soon. Apart from her talent, the star has also been in the spotlight thanks to her appearance, as side-by-side pics of Glaser's face make her plastic surgery transformation undeniable.

Glaser has also been a hot topic due to her on-and-off-again relationship with producer Chris Convy. The two met in 2013 thanks to the show "Nikki & Sara Live," and they have been in each other's lives since. However, multi-award-winning international wellness and relationship coach Teresha Young explains exclusively to Glam that their relationship has a handful of obstacles, raising serious questions about their future. "Some of the talking points around Nikki Glaser and Chris Convy's dynamic raise interesting questions rather than clear-cut red flags," she tells us. After more than a decade, Glaser and Convy are still together, but our expert believes that their issues might put a strain on their love.

Nikki Glaser has opened up about wanting her partner to see other people, while she doesn't really have an interest in seeing anyone but him. "I'm a weirdo, and I like my boyfriend to at least entertain the idea of being with other women or be with them," the comedian revealed to Graham Bensinger in 2022, adding that she wouldn't mind if Convy slept with other people. However, maintaining rules and boundaries in an open relationship can be very difficult, and Teresha Young stresses the importance of communication between partners.

"Glaser has previously shared that she's open to Convy seeing other women, as long as it doesn't become emotional," Young exclusively tells Glam. "These days, non-monogamous and open relationships are far more widely accepted, but they tend to work best when everyone is truly on the same page, with clear boundaries, regular communication, and ongoing check-ins, especially as emotional connection isn't always something that can be neatly controlled." While relationships like this can thrive and last for a long time, they can also crumble because of jealousy and resentment, especially if one partner isn't being honest about their feelings.

Removing yourself from the toxic on-again, off-again relationship cycle can be difficult, and while not all on-and-off again relationships are doomed, more often than not, they do point to some problems. While Nikki Glaser and Chris Convy began their relationship in the early 2010s, the comedian has revealed that they haven't really been stable. She shared on "The Howard Stern Show" in 2024, "Committing to anything forever, I think that 'forever' makes me think of no other adventures ... It's just kind of admitting defeat. It's settling."

Our relationship expert confirms that the couple's cycle may be due to fear of commitment. "Their on-again, off-again history may also point to a degree of uncertainty around long-term commitment," Teresha Young shares exclusively with Glam. "For some couples, that rhythm works well, but for others it can suggest differing ideas about permanence, security, and what the future should look like together." Considering that Glaser has revealed that she and Convy have ended their relationship "probably five times in 10 years," this red flag shouldn't be disregarded.

Given Nikki Glaser's profession, it's not uncommon for her to poke fun at the people closest to her. As a comedian, Glaser often looks for inspiration in everyday life, and naturally, her boyfriend is bound to end up being the center of a punchline here and there. During her "Saturday Night Live" monologue in 2025, Glaser poked fun at her boyfriend's height, saying, "He's 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 ... It's like getting a hot guy on discount. He's marked down." Of course, as height has become such a significant factor in dating, many would expect that the joke didn't land that well with Convy.

Teresha Young warns that jokes like these could affect the couple's relationship, especially if there is a lack of proper communication. "Repeated jokes about a partner, particularly those referencing appearance or worth, such as calling him a 'hot guy on discount,' can occasionally blur the line between playful and potentially diminishing if both partners aren't fully aligned on what feels comfortable," she shares exclusively with Glam. Specific jokes can particularly cause damage if one is already insecure about the traits mentioned. "Overall, the key to a dynamic like this is whether both partners keep communication open, honest, and respectful, and whether they continue to feel good about their boundaries as the relationship evolves," Young adds. 

Nikki Glaser and Chris Convy began dating prior to her big break, and while the dynamic between them was more balanced in the mid 2010s, today it's clear that Glaser is the more famous, rich, and powerful one among the two. In 2025, her net worth was estimated to be around $10 million, per Celebrity Net Worth, while little is known about Convy's finances. "When one partner's career is very much in the public eye or quickly gaining momentum, it can sometimes tip the balance, particularly if that success starts to feel like it comes with higher status or authority," Teresha Young exclusively tells us. "If this shows up through subtle put-downs, dismissive communication, one-sided decision-making, or moments where one person's needs and voice overshadow the other's, it can gradually chip away at emotional safety." 

In this case, depending on how Glaser treats him, Convy could easily feel like he's not worthy of her as a partner. Young clarifies that such behavior can cause the less traditionally successful partner to "feel comparatively less significant, or even a little smaller, within the relationship." She adds that this can result in "insecurity, self-doubt, or overly accommodating behavior, all of which can quietly disrupt a sense of equality and mutual respect."

Of course, just because one partner is considered more successful, that doesn't have to mean the relationship won't last. "In relationships where both people feel truly valued, respected, and secure, differences in career paths tend to matter much less," Young explains.