Whitney Cummings is engaged to professional skateboarder Chris Cole, and she has no idea where they are getting married. She might do it alone with him at Tokyo Disneyland. She might invite a thousand people to Dave and Buster’s.
She looked at the Madonna Inn, the famously pink boutique hotel in San Luis Obispo, and loved it completely. She considered an animal sanctuary until she decided her friends were too annoying to be trusted around horses.
She is shopping for her dress on eBay. Her two-year-old son Henry might walk her down the aisle. Her officiant might be comedian Bert Kreischer, shirtless.
Cummings, 43, opened up about all of it in an exclusive interview with PEOPLE at An Unforgettable Evening, a charity gala in Beverly Hills on March 11, 2026.
She hosted the event and spoke with her characteristic velocity, zigzagging between deeply sincere and spectacularly absurd in the same sentence, which is essentially the Whitney Cummings brand distilled into its purest form.
“Wedding planning is going pretty well,” she said, before immediately making clear that no part of it is going particularly well in any conventional sense. “I’m vacillating in between getting married at Tokyo Disneyland, like just the two of us, and a thousand people at Dave and Buster’s. I am so all over the place.”
Who Is Whitney Cummings?
Cummings was born September 4, 1982, in Washington, D.C. She grew up in Georgetown, graduated from the University of Pennsylvania with the intention of becoming a journalist, and instead moved to Los Angeles in 2004 and started doing stand-up comedy.
She appeared on MTV’s Punk’d, became a fixture on Chelsea Lately alongside Chelsea Handler, and built a reputation on the Comedy Central roast circuit where she roasted Joan Rivers, David Hasselhoff, Donald Trump, and others with the kind of precision that made it clear she was better at the job than most people doing it.
In 2011 she achieved something nearly unprecedented: she created and starred in her own NBC sitcom, Whitney, while simultaneously co-creating the CBS sitcom 2 Broke Girls with Michael Patrick King.
Having two shows on two different broadcast networks at the same time is the kind of thing that does not happen very often.
Whitney ran for two seasons and was canceled in 2013. 2 Broke Girls ran for six seasons across 138 episodes and remains one of the most financially successful syndicated sitcoms of the decade.
She has released six stand-up specials across Comedy Central, HBO, Netflix, and OnlyFans.
She directed the 2017 comedy film The Female Brain and published a memoir the same year, I’m Fine…And Other Lies, a collection of personal stories about codependency and emotional growth. She served as head writer and executive producer on the 2018 revival of Roseanne for ABC before leaving prior to the show’s cancellation.
Her podcast Good for You launched in 2019 and became one of the more substantive comedy podcasts in circulation, featuring comedians, neuroscientists, and experts across a wide range of fields.
She is currently on her Big Baby Tour in 2026, incorporating material about motherhood and identity.
When Did Cummings Get Engaged?
Cole, also 43, proposed to Cummings in late October 2025 during her daily hike in Topanga Canyon behind her Los Angeles house. TMZ published photos of the moment, showing Cole on one knee and Cummings kneeling in front of him with her hand covering her face.
She announced the engagement on the November 3, 2025 episode of her Good for You podcast, with characteristic ambivalence about the announcement itself.
“I got engaged last week and I don’t know how to tell anybody,” she told listeners. “I’m embarrassed to even talk about it and I’m trying to just get it out of the way.” She described the post-proposal moment as “awkward,” recalling that Cole had made no dinner reservations and suggested Pizza Hut when she asked what they should do next. “As soon as he got the ring on, he’s like, I never have to try and impress you again,” she said on the podcast. “And I was like, well, should we go get dinner or something?”
The ring itself has a story. It is from the Bayou jewelry line by actress and activist Nikki Reed, who created the sustainable jewelry brand. Cummings had borrowed the specific ring, called the Bayou ring, for a Fox television appearance.
When it came time to return it, Cummings negotiated instead. She traded Reed her beloved 1981 Chevrolet Silverado truck for the ring outright. Reed, apparently, loved the truck immediately and accepted. This is how Cummings acquired her engagement ring. It is not how most people do it.
Chris Cole is one of the most decorated professional skateboarders in the history of the sport.
He has been a multiple-time World Skateboarder of the Year, won numerous X Games medals, and has been a flagship athlete for brands including DC Shoes and Zero Skateboards across a career spanning more than two decades.
He and Cummings first went public as a couple in May 2025 and were photographed together at the ESPY Awards in July 2025.
The Wedding Planning
The PEOPLE interview at the Beverly Hills gala represents the most detailed public update Cummings has given on the wedding since the engagement.
It covers every major decision and reveals that essentially none of them have been made.
On the venue, after noting the Tokyo Disneyland to Dave and Buster’s spectrum she is navigating, she added, “I looked at Madonna Inn. It’s the most fantastic place I’ve ever been in my life. It’s all pink. So then I’m like, do I do it in an animal sanctuary because I’m an animal person? But my friends are too annoying. I won’t let them around horses. So I’m just trying to figure it out.”
On the guest list, she is not planning to set limits. “If you want a plus-one that you met on Hinge and she’s in your polyamorous throuple, bring them.
I don’t want to be saying no to people and stuff. Everyone’s welcome.” This philosophy makes headcount nearly impossible to calculate, which is contributing to the venue problem, which is contributing to everything else remaining unresolved.
On the officiant, she is considering having multiple people compete for the role, with comedian Bert Kreischer among those vying for it.
She described the possibility of Kreischer officiating in what she called “Chippendale style,” meaning shirtless with a bow tie. This is a plausible outcome based on everything Bert Kreischer has ever done publicly.
On the dress, she is deep in eBay. “You’d be surprised how many women buy never worn wedding dresses on eBay,” she said. “You’ll get a wild story and a very inexpensive never worn wedding dress.”
She noted that a never-worn Vera Wang can be found on the platform for around $1,000, down from its original retail price by a factor of many. She described this as helping women in difficult situations while also solving her own problem.
On the aisle, she is genuinely torn between two options, and the second one landed differently in the interview than she expected it to.
Her father died in 2013, which means the traditional father-escorting-daughter moment is not available to her. Henry, her two-year-old son who was born in December 2023, has emerged as one candidate to fill that role. “He might walk me down the aisle,” she said, before catching herselfm “I don’t have a dad, so I’m trying to… I did also want to have all… Oh, it’s going to make me cry.”
What she almost said was that she also wants all of her closest girlfriends walking beside her simultaneously, as a way of saying she is marrying Cole but she is also, in a sense, bringing everyone who supported her to get here.
“You’re marrying all of us,” is how she framed it. She noted that in past relationships, red flags included partners who did not get along with her friends, adding that she now understands what that meant.
What Is Cole Doing?
Cummings reserved some of her most enthusiastic energy for describing what Chris Cole has been contributing to the wedding planning. He has been practicing the lift from the final scene of Dirty Dancing.
“My fiancé is a famous skateboarder and he’s so physically talented because they’re basically ballerinas and I want so badly to do the Dirty Dancing, the end,” she said. “It’s actually hard. So we’re trying to choreograph that.”
The logic that a professional skateboarder is essentially a ballet dancer in terms of the body control and spatial awareness required is not wrong.
Whether it produces a successful Dirty Dancing lift at a wedding reception, at a venue that may or may not be a Dave and Buster’s, officiated by a shirtless Bert Kreischer, with the entire guest list including a Hinge date and possibly a throuple, wearing a dress purchased on eBay, while Henry walks down the aisle, remains to be seen.
Cummings was previously engaged to music artist Miles Skinner, which she announced in September 2018 and ended in February 2020.
She described the reason for that split as simply not being ready to plan a wedding. The planning she is doing now suggests she has found a solution to that particular problem, which is to approach the planning in a manner that makes the planning itself part of the entertainment.
