Comedian Whitney Cummings is engaged to professional skateboarder Chris Cole, but she says she feels a bit awkward sharing the big news. Whitney told fans on her “Good For You” podcast on Monday that she got engaged last week. “I got engaged last week, and I don’t know how to tell anybody,” she said. The proposal happened during one of her daily hikes in Topanga Canyon, right behind her Los Angeles home, two Sundays ago, according to TMZ.
Whitney Cummings shared that Chris Cole popped the question during the walk, and it totally surprised her. She even joked that she didn’t know what to do next. “I’m embarrassed to even talk about it,” she told her listeners with a laugh. “I’m just trying to get it out of the way.”
Whitney Cummings and Chris Cole’s surprise proposal in Topanga Canyon
In May, Whitney Cummings had told everyone that she was dating Chris Cole, a pro skateboarder known for his major wins in the sport. TMZ reported that Chris Cole proposed while they were hiking together, and Whitney didn’t expect it at all. The ring, as per TMZ, is from Nikki Reed’s jewelry line, Bayou.
After saying yes, Whitney admitted she and Chris Cole didn’t really know what to do next. On her podcast, she laughed and said that when she asked what they should do to celebrate, Chris suggested Pizza Hut. “I haven’t spoken to him since,” she joked, making her fans laugh too.
Whitney Cummings jokes about Pizza Hut after Chris Cole’s engagement surprise
Before dating Chris Cole, Whitney was engaged to Miles Skinner, a music artist. They were together for more than a year before breaking up in 2020. This new engagement comes almost five years later, and fans are happy to see her smiling again.
Whitney Cummings has always been open about her love life on her podcast and social media. Now, even though she says she feels shy talking about her engagement, she couldn’t hide her happiness.
Also Read: Tommie Jakes Cause Of Death: How Did The Apprentice Jockey Die At 19
According to TMZ, the couple has been spending more time together lately and enjoying quiet days in L.A. with Whitney’s pets.
Fans hope Whitney Cummings and Chris Cole will share more details soon, but for now, the comedian seems happy keeping it simple, just like the way she told the world, on her own show, in her own funny style.
Whitney Cummings shared that Chris Cole popped the question during the walk, and it totally surprised her. She even joked that she didn’t know what to do next. “I’m embarrassed to even talk about it,” she told her listeners with a laugh. “I’m just trying to get it out of the way.”
Whitney Cummings and Chris Cole’s surprise proposal in Topanga Canyon
In May, Whitney Cummings had told everyone that she was dating Chris Cole, a pro skateboarder known for his major wins in the sport. TMZ reported that Chris Cole proposed while they were hiking together, and Whitney didn’t expect it at all. The ring, as per TMZ, is from Nikki Reed’s jewelry line, Bayou.
Whitney Cummings Engaged to Pro Skateboarder Chris Cole | Click to read more 👇 https://t.co/08S33eq3b6 pic.twitter.com/FvZB4OR2wP
— TMZ Sports (@TMZ_Sports) November 3, 2025
After saying yes, Whitney admitted she and Chris Cole didn’t really know what to do next. On her podcast, she laughed and said that when she asked what they should do to celebrate, Chris suggested Pizza Hut. “I haven’t spoken to him since,” she joked, making her fans laugh too.
Whitney Cummings jokes about Pizza Hut after Chris Cole’s engagement surprise
Before dating Chris Cole, Whitney was engaged to Miles Skinner, a music artist. They were together for more than a year before breaking up in 2020. This new engagement comes almost five years later, and fans are happy to see her smiling again.
Whitney Cummings has always been open about her love life on her podcast and social media. Now, even though she says she feels shy talking about her engagement, she couldn’t hide her happiness.
Also Read: Tommie Jakes Cause Of Death: How Did The Apprentice Jockey Die At 19
According to TMZ, the couple has been spending more time together lately and enjoying quiet days in L.A. with Whitney’s pets.
Fans hope Whitney Cummings and Chris Cole will share more details soon, but for now, the comedian seems happy keeping it simple, just like the way she told the world, on her own show, in her own funny style.
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