Whitney Cummings has been engaged with her skateboarder boyfriend Chris Cole. She made the announcement of her engagement on her Good For You podcast episode which aired on November 3, 2025.She told her viewers:“I got engaged last week … and I don't know how to tell anybody. I'm embarrassed to even talk about it, and I'm trying to just get it out of the way.”Reports stated that Cole proposed to her during a hike in Topanga Canyon near her Los Angeles home. Her massive diamond ring is from Nikki Reed’s lifestyle brand called Bayou with Love. The proposal took place almost five months after they started dating.Chris Cole was born in Statesville in North Carolina. He spent his later years in Pennsylvania. Known for his technical skills, consistency and innovative tricks, he has built an impressive career in skateboarding.Continue to read more.All we need to know about the life of Chris Cole Chris Cole’s personal life has come into the spotlight following the news of his engagement to Whitney Cummings, which went viral online. The comedian first revealed her romance in May this year. She shared a joint post with the “skate god” where he taught her to ollie.He was previously married to Christine Flannigan with whom he shares two kids. She has publicly alleged that he subjected her and her children to domestic violence. She has detailed accounts of physical and emotional abuse at the hands of her former husband.However, Cole has denied her claims. In an Instagram story, he called the accusations “beyond shocking and categorically false.” He added:“As hard as it has been to hold off on commenting on the situation, I have kept silent because children are involved and this is obviously traumatic.” View this post on Instagram Instagram PostHe further added:“weaponizing and involving children is incredibly traumatic and unfair to them. If these accusations we're true they'd be handled in a court of law, not through court of public opinion and kids social media. I will make a statement when it won't further harm my kids.”In an interview with The Talks, Chris Cole opened up about how he learned discipline from his older brother, who was “bigger and smarter.” He said that when he was a kid, he always tried to be something. It later helped him become the world's best technical skateboarder.Chris Cole explained to The Talks that when he was young, he had a lot of energy. He took medication to sleep, so he had to release that energy some kind of way. He rode a bike and played on a football team, but skateboarding was everything.He started skating at the age of nine and gained notoriety as an amateur in San Fransico. He started his own brand of clothes Omit Apparel, and has partial ownership of Zero Skateboards. He once beat Paul Rodriguez Jr in the final round of Battle At The Berrics.Cole explained that, as a child, they did not have cellphones and no one could text anybody or find out where they were at that point in time. He stated that skateboarding was a sport which one could do alone and he enjoyed it thoroughly.In 2005, Chris Cole was awarded Thrasher‘s Skater of the Year, earning the title for a second time four years later. In the competitive arena, he yielded five X Games medals, victories in the Dew Tour, the Battle of the Berrics, the Maloof Money Cup Championship, the Copenhagen Pro, and in Street League Skateboarding.