Whitney Cummings got engaged to Chris Cole in 2025. The comedian recalled how the proposal left her feeling 'awkward.'
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Add BollywoodShaadis on GoogleWhitney Cummings is one of the most well-known comedians and actors. She is currently hogging the spotlight after Netflix streamed a special of the Mark Twain Prize for American Humor on Tuesday, July 21, 2026. Notably, Whitney, who hosted the comedy awards, had made a joke about President Donald Trump that didn't make it into the final cut.
Whitney claimed that she didn't really care that the joke was cut, as it had already been leaked beforehand. Amid the buzz, many have grown curious about the comics’ personal life. If you are one of them, let us introduce you to Whitney Cummings’ fiancé, Chris Cole.
According to reports, Whitney Cummings’ fiancé, Chris Cole, is a professional skateboarder. He is well known for his impressive skills and contributions to the sport. He was born on March 10, 1982, in Statesville, North Carolina. Some of his top tricks that he has gained recognition for include the 360 flip, Switch Frontside flip, and Backside 360 ollie down the staircase at Walkenberg High School in San Francisco.
It is worth mentioning that Chris was previously married to artist and tattoo enthusiast Christine Flannigan. They tied the knot in 2007 and have two children together: son Wyatt Cole and daughter Penelope Cole.
Chris and Whitney’s relationship first became public in August 2024 when the latter left a comment on one of Chris’s skateboarding clips on Instagram. She wrote, “There goes my baby,” to which he replied with a bunch of kissing emojis. Since then, the couple had appeared together in various public events, confirming their romance.
Later, Chris had also shared a heartfelt birthday message for his then-girlfriend on September 4, 2024. Taking to his Instagram Stories, he wrote, “It's my lady’s birthday! What I tell anyone who says “omg I love her” is that you only know 10 percent of why you should love her. She is so much more magical than she even knows. Simply the best.”
Reportedly, Chris and Whitney had begun dating in mid-2024 but had decided to keep it private until August of the same year. A year later, on the November 3, 2025, episode of her podcast Good for You, Whitney left fans shocked when she revealed that she got engaged a week ago and didn't know how to tell anybody. She claimed that she was “embarrassed to even talk about it,” and is “trying to just get it out of the way.
According to reports, Chris had proposed to her during her daily hike in Topanga Canyon, which is located behind Whitney’s LA home. A photo from the moment showed the skater down on one knee with Whitney kneeling in front of him, overwhelmed with emotion and covering her face. Recalling how the proposal had left her “surprised,” she said:
"It's so awkward. I was like, 'Okay, cool. Now what?' And I was like, 'Should we go to dinner or something?' He [Cole] had no plan afterward. As soon as he got the ring on, he was like, 'I never have to try to impress you again.'"
As of now, neither Chris nor Whitney has opened up about when exactly they plan to get married. However, the comedian revealed that wedding planning has already begun. In March 2026, Whitney said that she is still trying to figure things out, but is definitely working on it. She was quoted as saying:
"Wedding planning is going pretty well. I'm vacillating in between getting married at Tokyo Disneyland, like just the two of us, and a thousand people at Dave & Buster's. I am so all over the place."
What are your thoughts on Whitney Cummings’ fiancé, Chris Cole, and their relationship? Let us know.
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