Comedian and actress Whitney Cummings has stepped into a new chapter of her life with the joyful announcement of her engagement to professional skateboarder Chris Cole. The news comes with the same blend of humor and heart that fans have come to expect from the Los Angeles based entertainer.
Whitney shared the story on her podcast Good for You revealing that Chris proposed during a peaceful hike in Topanga Canyon near her Los Angeles home. The moment, she said, was both deeply touching and amusing in the way only real life can be. There was no grand staging or glamorous setup, just two people in love surrounded by nature. True to her comedic roots she joked that after the proposal Chris suggested they celebrate with a casual trip to Pizza Hut. Listeners laughed but also heard the sincerity in her voice as she described how right the moment felt.
The couple first made their relationship public in May 2025 after months of speculation from fans who noticed their growing closeness on social media. Cole, a respected figure in the world of professional skateboarding, is known for his grounded personality and quiet confidence, qualities that seem to perfectly balance Whitney’s sharp wit and lively energy. Friends of the couple say their chemistry is undeniable and that they share a deep mutual respect for each other’s careers.
For Whitney this engagement comes after a period of personal growth and reflection. She welcomed her first child, a son, in December 2023 and has often spoken about how motherhood has shifted her priorities and given her new perspective on love and partnership. In recent interviews she has emphasized the importance of choosing someone who feels like home and who understands the rhythms of her life both on and off the stage.
Their engagement marks a fresh beginning for the pair and it feels entirely fitting that it happened in Los Angeles, the city where Whitney built her career and found her comedic voice. It is also where she has found, it seems, a true partner who matches her passion and her humor. Fans across the entertainment world are celebrating the news and sending messages of love and congratulations.
As Whitney continues to balance motherhood, comedy, and now wedding planning, one thing is certain. The woman who has made millions laugh with her honesty and humor has found a reason to smile a little brighter herself. In her own words, love does not need to be perfect, it just needs to be real, and in that spirit she is embracing every imperfect, funny, beautiful moment that comes next.
