Who was Whitney Cummings ex-fiance? What we know amid comedian’s engagement to skateboarder Chris Cole

Whitney Cummings is engaged to professional skateboarder Chris Cole. The comedian announced her engagement on the November 3 episode of her podcast, Good for You, stating:

"I got engaged last week … and I don't know how to tell anybody."

She continued:

"I'm embarrassed to even talk about it, and I'm trying to just get it out of the way."

Cummings was previously engaged to Miles Skinner for more than a year before they separated in 2020. They met online, the Female Brain director revealed during an appearance on Conan in November 2017.

The couple got engaged in September 2018. Cummings shared the moment on her Instagram handle, where she appeared visibly shocked by the proposal.

"Today I got engaged. I handled it great! This just goes to show that if you work on yourself, trust your gut, and keep your ego in check you too can find love on a dating app," she captioned the post.

A year later, on November 7, 2019 interview with US Weekly, Cummings revealed that she had decided to put her wedding plans on hold:

"Yeah, Yeah, you know, it’s stressful. With everything that’s going on, it’s expensive. I don’t want to be that person who does the ‘sponsored’ wedding and like have to do that … I’m trying to find a way to do it. We’ll see."

However, on the February 5 episode of her podcast, Cummings revealed that her engagement had come to an end.

"I am not wearing an engagement ring. I am no longer engaged. Nothing nasty, no drama. It just wasn't — I feel like nobody will believe me — I truly just was not ready to plan a wedding, the whole thing really overwhelmed me," she said.

According to his LinkedIn, Miles is a film producer and has been working as a Creative Director and a Strategist since 2020. Graduating from Parsons School of Design - The New School with a Bachelor of Arts - BA, Communication and Media Studies, he has previously worked as a creative and art director for multiple companies.

Chris Cole proposed to Whitney Cummings on her daily hike

TMZ shared the Whitney Cummings proposal picture, reporting that it happened during her daily hike in Topanga Canyon behind her Los Angeles house. The picture featured Cole down on one knee while Cummings knelt with her hands on her face, visibly shocked.

Cummings described the moment as "awkward" in the aforementioned podcast, stating:

"It's so awkward. I was like, 'Okay, cool. Now what?' " she recalled. "And I was like, 'Should we go to dinner or something?' He [Cole] had no plan [for] afterwards."

She continued:

"As soon as he got the ring on, he was like, 'I never have to try to impress you again.' "

She further shared how she knows how she's "in love":

"You don't know you're in love until you act a different way than you've always acted with everybody else and you're like, 'Why am I so sensitive? Why do I care about this? Oh, I guess I'm, like, in love.' "

The full podcast is available on Whitney Cummings' official YouTube channel.