Whitney Cummings details unique engagement ring story ahead of wedding to Chris Cole

Comedian Whitney Cummings is sharing heartfelt details about her upcoming wedding to professional skateboarder Chris Cole, including the special role her 2-year-old son Henry may play in the ceremony.

Speaking exclusively to People at the annual An Unforgettable Evening breast cancer research fundraiser in Beverly Hills on March 11, the 43-year-old comedian revealed that her young son could have a meaningful part in the celebration.

“He might walk me down the aisle,” Cummings said, explaining the emotional reason behind the idea. “I don’t have a dad,” she added, referencing the loss of her father in 2013.

Cummings welcomed her son Henry in December 2023 and has said she and the child’s father are not together but co-parenting. 

The comedian announced her engagement to Cole, 44, in November 2025.

While the wedding is still in the planning stages, Cummings admitted she has yet to finalize many details, including where the ceremony will take place or how big the celebration will be.

“I’m vacillating between getting married at Tokyo Disneyland, just the two of us, and a thousand people at Dave & Buster’s,” she joked. “I am so all over the place.”

At one point, she even considered having her closest friends accompany her down the aisle. 

“I did also want to have all my girlfriends walking me down the aisle like you’re marrying all of us,” she said, referencing the idea that a partner becomes part of an entire friend group.

However, Cummings quickly realized that might be complicated. “I have too many girlfriends for that,” she added.

Among the venues she has considered is the colorful California boutique hotel Madonna Inn, which she described as “the most fantastic place I’ve ever been in my life.”

Still, other ideas have crossed her mind, including hosting the wedding at an animal sanctuary, reflecting her love of animals.

When it comes to her wedding dress, the comedian is also thinking outside the traditional bridal route. 

She revealed she’s been browsing secondhand gowns online, particularly on eBay.

“You’d be surprised how many women buy never-worn wedding dresses on eBay,” she said. “You can get a Vera Wang never-worn wedding dress for a thousand dollars.”

Cummings also shared the unusual story behind her engagement ring — a piece from actress and jewelry designer Nikki Reed’s collection.

The comedian originally borrowed the ring for a television project but quickly fell in love with it. 

Instead of returning the piece, the pair eventually worked out an unconventional trade.

Cummings gave Reed her vintage 1981 Silverado truck, a vehicle she had purchased during the pandemic, in exchange for the ring.

“She said it was the car she had always wanted,” Cummings recalled. “So I said, ‘Great news. This is your dream car, and this is my dream ring. You can have the car, and we’re even.’”

The experience has apparently inspired a new mindset for wedding planning.

“I’m kind of into bartering for my wedding,” Cummings joked.