Nikki Glaser's Rollercoaster Romance with Chris Convy

It’s a tale filled with humor, heartbreak, and healing. The comedian whose jokes leave audiences in splits is living a love story that’s been anything but conventional. Nikki Glaser and her boyfriend, Chris Convy, have had a rollercoaster relationship spanning over a decade. Their journey is a testament to enduring love powered by truth and humor.

A Reluctant Beginning

Nikki and Chris first crossed paths in 2013 on the set of “Nikki & Sara Live.” Nikki found herself drawn to Chris, but feared his lively spirit was fueled by substances. Her misgivings dissipated when she discovered his sobriety, turning her fondness into a real crush. As Glaser put it, “It was very Jim and Pam from The Office.”

The Growing Pains

Their relationship has been punctuated by various splits—“probably five times in 10 years,” according to Nikki. Around their early years, Nikki wrestled with the fear of permanent commitment, making her rethink the definition of settling. Yet each breakup taught them something new, eventually making them stronger.

The Big Move Back to St. Louis

In 2020, amid the COVID pandemic, Nikki returned to her roots in St. Louis. Collaborating on her E! docuseries became a turning point, with Chris willing to be filmed for the show—a gesture that, to Nikki, symbolized his love. As stated in Us Weekly, this era marked significant growth in their relationship.

An Open Book on SiriusXM

By 2024, Nikki’s candid revelations on SiriusXM’s The Howard Stern Show offered much insight into their relationship hurdles. Misunderstandings bred from her comedic confessions were dispelled, paving the way for newfound honesty and balance, thanks to Chris’s unwavering support.

Joking Through Life

In June 2025, Nikki revealed to People Magazine the complexities of working comedy into their relationship. “He’s so cool,” she said, and his green light to bring their life on stage as long as it’s humorous reflects their mutual understanding and trust.

The Height of Comedy

October 2025 saw Glaser take center stage at SNL. With her characteristic wit, she turned personal anecdotes into comedic gold, lightly jabbing at her boyfriend’s height with, “I met my boyfriend at TJ Maxx, clearance rack.” Her ability to spin personal stories into humor underscores their unique bond and shared sense of levity.

Through ups and downs, breakups and reunions, Nikki Glaser and Chris Convy remind us that love—with all its complexities—is most beautiful when embraced authentically.