Whitney Cummings announced on the November 3, 2025 episode of her popular podcast, “Good For You With Whitney Cummings, that she got engaged last week and has been keeping it a secret this whole time!
TMZ says the comedian, who boasts 1.8 million Instagram followers that include Lindsay Lohan, Demi Moore, and Reese Witherspoon, told viewers she didn’t “know how to tell anybody.”
So who is Whitney Cummings engaged to? Read on for details and check out the podcast episode below. She starts talking about the proposal around the 1:12:48 mark.
Whitney Cummings Is Engaged to a Pro Skateboarder
Cummings’ fiancé is Chris Cole, a professional skater TMZ says proposed to the social media star while she was taking her daily hike behind her L.A. area home. The proposal went down two Sundays ago, per the outlet.
The story also dished that the ring is from the jewelry line Bayou, by “Twilight” actress Nikki Reed. Reed played the blonde older sister of Edward Cullen in the smash hit teen romance films.
GettyWhat Whitney Cummings Said About Her Engagement
“I got engaged last week, and I don’t know how tell anybody,” said the 43-year-old before bursting into giggles. She went on, “I’m embarrassed to even talk about it and I’m just trying to get it out of the way.” She also said her fiancé successfully took her by surprise, but afterwards she felt awkward, wondering, “Now what?”
The comedian, who once appeared on MTV’s “Punk’d,” recalled that Cole failed to make any dinner plans, and suggested Pizza Hut when she asked if they should go out. “I haven’t spoken to him since,” she joked. Still, she insisted she’s in love with her new fiancé.
“You don’t know you’re in love until you act a different way than you’ve always acted with everybody else, and you’re like, ‘Why am I so sensitive? Why do I care about this?’ And then you’re like, ‘Oh, I think I’m just in love.'”
Fans Congratulated Whitney Cummings On Her Engagement
Viewers of the “Good For You” podcast filled the comments with congratulatory messages. One wrote, “CONGRATULATIONS!!!!!! I hope you allow yourself to feel the fullness of all the love and happiness you deserve and that is to come with your engagement and start of a new chapter together.”
Another said, “Loving this chapter of your life and comedy. You’re taking the power back from pain and loss and it’s admirable. I just lost both of my parents at 35 and only a year earlier lost my husband in an accident, no siblings, so I relate to your story and journey. I’m proud of how you have pushed forward, you only get better with time.”
