Whitney Cummings Engaged to Pro Skateboarder Chris Cole

Comedian Whitney Cummings announced her engagement to professional skateboarder Chris Cole during her podcast, "Good For You," sharing that the proposal took place during a daily hike in Topanga Canyon near her Los Angeles home. Despite her happiness, Cummings expressed feeling awkward and embarrassed about announcing the news, joking about the awkwardness following the proposal when Cole suggested celebrating with dinner at Pizza Hut, a suggestion she found surprising and disappointing. The engagement ring came from Nikki Reed's jewelry line, Bayou, and the couple had only been publicly dating since May. Cummings previously was engaged to Miles Skinner, but they split in 2020. She humorously recounted her surprise and uncertainty about what to do after saying yes, highlighting the intimate and informal nature of their celebration. Fans have responded positively to the news, happy to see Cummings smiling again and sharing her personal life openly.