Comedian Whitney Cummings is offering a glimpse into her highly unconventional wedding planning process with fiancé Chris Cole, revealing a range of potential venues from the whimsical to the wildly unexpected. From a fairytale celebration at Tokyo Disneyland to a high-energy party at Dave &. Buster’s, Cummings is embracing a playful approach to her upcoming nuptials, alongside some equally surprising details about her engagement ring and potential aisle escort.
The 43-year-old comedian shared her wedding brainstorming during an appearance at An Unforgettable Evening charity gala, as reported by People magazine. Cummings’ openness about the planning process highlights a desire for a celebration that truly reflects her personality and relationship with professional skateboarder Chris Cole, who she announced her engagement to in November 2025.
Venue Visions: Disneyland Dreams and Dave & Buster’s Blowouts
Cummings admitted to being “all over the place” when it comes to choosing a location for the ceremony. The initial idea of a small, intimate wedding at Tokyo Disneyland, just the couple, quickly morphed into a vision of a much larger celebration, potentially hosting up to 1,000 guests at Dave & Buster’s. She also explored other unique options, including the famously pink Madonna Inn in California and an animal sanctuary, though concerns about her “annoying friends” behaving around horses ultimately ruled out the latter.
The comedian’s difficulty in settling on a venue stems from her genuine affection for multiple locations and a self-described inability to exclude anyone from the guest list. “I refuse to turn anyone away,” Cummings explained, making a precise headcount a significant challenge.
A Dirty Dancing Moment and Unconventional Guest List Policies
Beyond the venue, the couple is planning a show-stopping reception performance. Chris Cole has been diligently practicing the iconic lift from the movie Dirty Dancing, with Cummings playfully noting that skateboarders are “basically ballerinas.” The couple is committed to mastering the choreography for a memorable moment on their big day.
Cummings is also embracing a decidedly inclusive guest list policy. As she stated in a quote widely circulated online, “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.”
Ring Trade and Aisle Walk: Personal Touches and Emotional Significance
The engagement ring itself has a unique story. Cummings bartered for the piece, trading a 1981 Silverado truck to Nikki Reed for a ring from her collection – specifically, the Bayou ring. She initially borrowed the ring for a Fox television appearance and, upon its return, negotiated a permanent exchange with Reed, who reportedly loved the truck.
Adding another layer of emotional depth, Cummings is considering who will walk her down the aisle. Having lost her father in 2013, she is contemplating having her 2-year-old son, Henry, fulfill the traditional role. Alternatively, she is also considering being escorted by all of her girlfriends, a gesture symbolizing the importance of her female friendships and a desire to “marry all of them,” not just Cole.
As Whitney Cummings and Chris Cole continue to plan their wedding, their unconventional choices and open approach are captivating fans. The couple’s willingness to embrace the unexpected and prioritize personal meaning promises a celebration that will be anything but ordinary. The next steps for the couple involve finalizing the guest list and, of course, perfecting that Dirty Dancing lift.
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