Whitney Cummings Engaged to Chris Cole | Proposal Story, Podcast Reaction & Career Highlights
Comedian and actress Whitney Cummings has some exciting news — she’s officially engaged! The 43-year-old revealed on the November 3 episode of her podcast Good for You that her longtime boyfriend, professional skateboarder Chris Cole, popped the question during one of their daily hikes in Topanga Canyon, Los Angeles.
“I got engaged last week … and I don’t know how to tell anybody,” Cummings laughed. “I’m embarrassed to even talk about it, and I’m trying to just get it out of the way.”
The surprise proposal came as a complete shock to the comedian, who described the moment as “awkward” yet sweet. “It’s so awkward. I was like, ‘Okay, cool. Now what? Should we go to dinner or something?’” she recalled.
The Proposal: Whitney Cummings Engaged to Chris Cole
Chris Cole got down on one knee during their scenic hike behind her Los Angeles home. The touching moment was captured in photos showing Whitney covering her face, visibly emotional.
When Whitney asked Cole how they should celebrate afterward, he jokingly suggested Pizza Hut.
“He’s never pitched Pizza Hut before in his life,” Whitney said on her podcast. “I haven’t spoken to him since!”
Fans immediately loved the story, calling it the most “Whitney Cummings way to get engaged ever.”
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A Sparkling Ring with a Personal Connection
Reports say that the engagement ring was designed by Twilight star Nikki Reed’s jewelry line, Bayou, which focuses on eco-friendly and ethical craftsmanship. The ring’s elegant simplicity perfectly matches Whitney’s grounded and witty personality.
Who Is Chris Cole?
Chris Cole, 43, is a world-renowned professional skateboarder celebrated for his technical skill, creativity, and championship record — including multiple X Games gold medals. He’s respected in the skating community for his consistency and influence on the sport.
The couple began dating publicly in May 2025, though they’d kept their relationship relatively private until now. Fans have since spotted them together at the 2025 ESPY Awards and on Whitney’s podcast.
From Comedy Clubs to Hollywood: The Story of Whitney Cummings
Whitney Cummings (born September 4, 1982, in Washington, D.C.) is not just a comedian — she’s one of the most accomplished women in modern comedy.
After graduating magna cum laude from the University of Pennsylvania in 2004 with a degree in Communications, she moved to Los Angeles to pursue entertainment. She began performing stand-up and soon earned recognition as one of Variety’s “10 Comics to Watch” in 2007.
Her career quickly took off as she became a regular on Chelsea Lately and participated in Comedy Central Roasts of Joan Rivers, David Hasselhoff, and Donald Trump.
In 2011, Cummings co-created the hit sitcom 2 Broke Girls with Michael Patrick King, and also starred in her semi-autobiographical series Whitney. Though Whitney only ran for two seasons, it helped her develop as a creator, writer, and producer.
She made her directorial debut with The Female Brain (2017) and later published her book I’m Fine… And Other Lies — an honest look into her personal struggles and growth.
Cummings has since become a leading voice in modern comedy, known for her Netflix special “Can I Touch It?” (2019), which introduced her look-alike robot, and her hit podcast Good for You, launched in 2019.
Whitney Cummings Journey Through Challenges
Cummings has spoken openly about growing up in a dysfunctional household in Washington, D.C., where her parents divorced when she was five. Despite a difficult childhood, she pursued excellence in school and entertainment, using humor as both a shield and a source of empowerment.
Over the years, she’s discussed dealing with overwork and an eating disorder during her early career, experiences that shaped her resilience and perspective on mental health.
Love, Motherhood, and New Beginnings
Before her relationship with Chris Cole, Whitney was engaged to creative director Miles Skinner, but the pair ended things in 2020.
In December 2023, she welcomed her first child, a son named Henry, whom she affectionately introduced as her “sweetest little piglet.” Motherhood, she says, changed her in ways she didn’t expect — making her softer, funnier, and more grateful.
Now, nearly two years later, her engagement marks a beautiful new chapter filled with love, laughter, and balance.
Fans React to the Engagement
After sharing the story on her podcast, Whitney’s fans filled social media with congratulatory messages — and plenty of Pizza Hut jokes. One fan wrote, “Only Whitney could make an engagement story sound like stand-up material.”
Her unfiltered humor and genuine personality continue to make her one of the most relatable figures in Hollywood.
What’s Next for Whitney and Chris?
While Whitney hasn’t shared any wedding plans yet, her fans are already eager to see what kind of celebration she’ll have — though knowing her, it may include laughter, friends, and maybe even a pizza box centerpiece.
For now, the comedian seems content simply enjoying the joy of the moment — and sharing it with her audience in true Whitney fashion: honest, funny, and heartfelt.
Whitney Cummings has spent her career turning life’s chaos into comedy. Now, as she steps into this new chapter with Chris Cole, it’s clear that love — like comedy — is best when it’s genuine, surprising, and a little awkward.
