Charissa Thompson’s Dating History: What to Know About Her Ex-Husbands, Current Boyfriend

Fox Sports reporter Charissa Thompson has earned the love of fans with her bubbly personality and sports expertise. The newscaster has shared details about her love life and past relationships on the “Calm Down” podcast with Erin Andrews. Keep scrolling to learn more about her dating history, her past marriages and her current boyfriend. 

How Many Times Has Charissa Thompson Been Married?

Charissa has been married twice. She walked down the aisle for the first time at the age of 25, though most of the details about her first marriage have been kept pretty private. In an April 2016 Facebook post, the former ESPN host gave a rare shout-out to her former spouse for helping her through a difficult time.

“When your ex-husband helps you through sadness and makes you smile,” she captioned a photo with him. “He’s a hot mess and I appreciate him so much. Ladies, by the way he’s single! I’ll hook you up.”

Charissa announced her engagement to Kyle Thousand in a now-deleted Instagram post in January 2020. She revealed that she married her second husband in February 2021 on Instagram. The broadcaster shared several photos from their intimate gathering in Scottsdale, Arizona, for her fans to see on social media.

“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,” the TV personality penned. “So, a huge thank you to those that (were there) and made this day so special and (those that weren’t there) who still made us feel so loved.”

In April 2022, Charissa filed for divorce from her spouse citing “irreconcilable differences” as the cause of their split. They did not welcome any children together during their union. 

Who Is Charissa Thompson’s Ex-Husband Kyle Thousand?

Kyle is a sports agent who had a brief college baseball career. After graduating from Creighton University School of Law in 2007, the attorney joined Katten Muchin Rosenman LLP. A few years later, he joined the team at Excel Sports Management before being named the managing director of baseball at Roc Nation. In December 2022, Kyle announced on Instagram that he became the head of baseball for Milk & Honey, an entertainment and sports management company. 

Charissa opened up about her split from the sports mogul during an episode of her podcast in April 2022.

“I had a s–tty week,” the Washington native said. “The news of my pending divorce came out and it’s obviously not something that I wanted at all as somebody who grew up in a family — my parents were married since [they were] 18. I trust in the institution and I’m somebody that’s been married and divorced before, so when I got married the second time, I was so hopeful that it would be what you stand up there and say it will be, which is, forever, for better or for worse and all the things.”

She continued, “I am embarrassed to admit that this is now my second divorce at 40.” While getting candid during the episode, Charissa received support from Erin as she looked toward the next chapter of her life.

Who Is Charissa Thompson Dating?

In July 2022, Charissa shared a video montage from a trip to the Amalfi Coast with her boyfriend, Steven Cundari, on Instagram. In several of the clips, the pair shared smooches and cuddled up as they took in the stunning ocean views. On his Instagram account, the businessman posted a photo with his girlfriend in coordinating green outfits from the trip. 

During a September 2022 episode of her podcast, Charissa confided in Erin about a funny moment she shared with Steven at home. When the marketing executive asked Charissa to borrow one of her duffel bags for a trip, she panicked thinking she left something “embarrassing” behind in the bag. After creating a diversion, the news reporter ​​was able to search the bag and found $100. Charissa and her cohost laughed at the experience.

“New relationships are fun and exciting! But they also come with some challenges … Especially when you’re hiding a thing or two,” Charissa wrote on Instagram after the funny moment with her beau.