Comedian Nikki Glaser and her boyfriend, Chris Convy, have maintained a decades-long on-again, off-again relationship. Their journey began in 2013, when they worked together on Glaser's MTV show, Nikki & Sara Live. Convy, a producer on the show, initially sparked Glaser's interest with his confidence and humor.

Their early relationship evolved amidst professional highs and lows. Convy went on to produce Glaser's 2016 comedy series, Not Safe with Nikki Glaser, which unfortunately only ran for one season. This, like many relationships, faced its challenges. Glaser later admitted that her candid approach to expressing her feelings through her podcast, sometimes without direct communication with Convy, strained the relationship.

However, the couple persevered. Through difficult periods, Glaser's reflections on their relationship highlighted the commonality of temporary challenges in both professional and personal endeavors. The Covid-19 pandemic and their return to St. Louis, Missouri, played a role in strengthening their bond, with Glaser expressing her desire for a more committed future. Their journey culminated in a renewed appreciation and commitment to their relationship.

Despite past conflicts, Glaser and Convy appear to be closer than ever, with Glaser affirming their enduring love on the Howard Stern show. This demonstrates the resilience of their relationship in the face of obstacles.

Interestingly, Glaser's past relationships also involved other comedians. While she briefly connected with comedian Pete Lee, the timing was not right. A similar pattern emerged in her brief romance with comedian Mike Recine, where differing expectations led to the relationship's end.