Charissa Thompson is a name synonymous with the high-energy world of sports broadcasting. But there’s another field where fans are equally invested—her love life. From matchmaking escapades to candid revelations on her podcast, Thompson’s journey of love is anything but conventional. What’s the latest buzz about her boyfriend and past relationships? Buckle up; it’s time to dig into her rollercoaster romantic life.  

Who is Charissa Thompson’s boyfriend?

Charissa Thompson’s current boyfriend, Steven Cundari, didn’t just walk into her life; he was handpicked by none other than her close friends Matthew and Kelly Stafford. Yes, the Los Angeles Rams quarterback and his wife decided they’d had enough of Thompson’s “loser” dating streak.  

On her Calm Down podcast with co-host Erin Andrews, Thompson spilled the details of her friends’ matchmaking prowess. “Matthew and Kelly were sick of me dating losers and they were like, ‘We have a great guy for you.’ So they were the matchmakers. It was vetted. I know the social security and the bank account now, so all is right.” Andrews, not one to hold back, added her glowing approval. “I basically call him her husband because I’m thinking it into existence.”

Thompson’s relationship with Cundari became public in July 2022 when she posted a dreamy video of their Amalfi Coast getaway. Shortly after, Cundari matched the vibe with an Instagram post of the duo in green, color-coordinated outfits.  

The relationship isn’t just romantic—it’s downright hilarious. Thompson shared one story where Cundari asked to borrow her duffel bag for a trip. In a panic, she rummaged through the bag fearing she’d left something embarrassing inside. Only to find a $100 bill instead! LOL! Reliving the moment on her podcast, Thompson couldn’t stop laughing.  

Her dating history? Yeah, that also includes a high-profile relationship with Jay Williams from 2013 to 2015, a former college basketball player and ESPN analyst! Not bad huh? But things fizzled out, and Williams moved on to marry Nikki Bonacorsi.  

Is Charissa Thompson married?

As much as fans want a fairy tale ending for Thompson, she isn’t married—at least, not right now. The sports presenter has been through two marriages, both of which ended in heartbreak.  

Her most recent marriage was to sports agent Kyle Thousand. The couple got engaged in early 2020. And soon enough, tied the knot in an intimate ceremony. Thompson had shared her excitement at the time, “The day was perfect. Sadly, we couldn’t invite all our friends and family due to COVID, but we didn’t want to wait any longer to start our lives together.”  

But it wasn’t happily ever after! In April 2022, Thompson filed for divorce, citing irreconcilable differences. One can only imagine the emotional toll about which she opened up on her podcast. “The news of my pending divorce came out, and it’s obviously not something that I wanted at all. I grew up in a family where my parents were married since they were 18. I trusted the institution of marriage.”

Thompson’s first marriage at 25 remains a mystery, as she’s only spoken fondly of her ex-husband. In a playful Facebook post in 2016, she even tried setting him up with others, joking. “He’s single! I’ll hook you up.”

From her failed marriages to her current relationship with Steven Cundari—facilitated by matchmaking friends—it’s a story of resilience, humor, and hope. Whether she’s sharing awkward duffel bag stories or receiving public encouragement to marry again, Thompson’s journey of love is as lively as her broadcasting career. Fans can’t wait to see what’s next for this NFL superstar—both on the field and in her heart.