The Shocking Truth About Whitney Cummings’ Fiancé: 5 Things To Know About Skateboarder Chris Cole

The search for Whitney Cummings' "boyfriend" has a definitive and exciting new answer as of late 2025: she is officially engaged! The famously candid comedian, known for her sharp wit and refreshingly transparent discussions about relationships and dating, has confirmed that her partner, professional skateboarder Chris Cole, proposed in a surprising and intimate fashion. This update marks a significant new chapter for Cummings, who has previously been vocal about her skepticism toward traditional marriage, making the news of her engagement to Cole a major talking point in the comedy and entertainment world. This article dives deep into the details of their relationship, provides a full profile of her new fiancé, Chris Cole, and explores the comedian's journey from a self-proclaimed commitment-phobe to a newly engaged woman. We have the freshest details about the proposal and a complete look at Whitney Cummings' multifaceted career.

Whitney Cummings: A Full Biography and Professional Profile

Whitney Cummings is a prolific American stand-up comedian, actress, writer, director, producer, and podcaster. She is one of the most recognizable voices in modern comedy, consistently tackling sensitive and taboo topics with a unique blend of humor and intelligence.

• Full Name: Whitney Ann Cummings
• Date of Birth: September 4, 1982
• Place of Birth: Washington, D.C., U.S.
• Education: University of Pennsylvania (graduated 2004)
• Known For: Stand-up comedy specials (e.g., *I'm Your Girlfriend*, *Can I Touch It?*), creating the sitcoms *Whitney* (2011–2013) and *Two Broke Girls* (2011–2017).
• Current Projects: Hosting the popular podcast *Good for You*, touring extensively with new stand-up material, and directing.
• Relationship Status: Engaged to Chris Cole (as of late 2025).
• Key Themes in Work: Gender dynamics, dating and relationships, technology's impact on intimacy, and self-help culture.

The New Fiancé: Who is Chris Cole?

The man who captured the heart of the famously independent comedian is James Chris Cole, a legend in the world of professional skateboarding. Their relationship, which became public in August 2024, has been a source of fascination for fans, given their seemingly different worlds—stand-up comedy and extreme sports.

1. He is a Two-Time "Skater of the Year"

Chris Cole is not just a casual skateboarder; he is a highly decorated professional. Born on March 10, 1982, in Langhorne, Pennsylvania, he is a two-time recipient of the prestigious *Thrasher Skater of the Year* award, winning in 2005 and again in 2009. This achievement places him in an elite class of athletes. He has been a professional since 2000, first turning pro for Jamie Thomas's company, Zero Skateboards.

2. The Proposal Was a Complete Surprise on a Hike

In a moment that perfectly blends the intimate with the unexpected, Chris Cole proposed to Whitney Cummings during her daily hike in Topanga Canyon, located behind her Los Angeles home. Cummings announced the engagement on her *Good for You* podcast, admitting she was completely blindsided by the proposal. She joked that she was so surprised she didn't know what to do afterward, a relatable moment of flustered joy for someone who usually has a joke for every situation.

3. He Brings an Unexpected Entity to Her Life

Cummings has often used her stand-up and podcast to discuss her dating life, which often involved men in the entertainment industry. Chris Cole, as a professional athlete in the world of skateboarding, represents a significant departure from her typical romantic partners, such as her previous relationship with filmmaker Peter Berg or her former engagement to Miles Skinner. The pairing of a sharp-tongued comedian and a grounded, world-renowned action sports athlete has proven to be a surprisingly perfect match, highlighting that love often comes when you least expect it and from unexpected places.

4. He is a Key Entity in the Skateboarding World

Cole's career entities extend beyond just awards. He is known for his technical skill, resilience, and dedication, having been sponsored by major brands like DC Shoes, Fallen Footwear, and Monster Energy over the years. His influence is global, making him a major figure and a respected entity within the international skateboarding community. This level of professional dedication aligns well with Cummings' own intense work ethic in the comedy world.

5. The Engagement Follows a Previous Called-Off Wedding

This engagement is particularly meaningful as it follows a previous engagement to Miles Skinner, which Cummings called off in 2020. She has been candid about her struggles with commitment and her previous fear of marriage. Her willingness to take this step with Chris Cole suggests a profound shift in her perspective on love and partnership, moving past the anxiety that surrounded her previous attempt at marriage. The comedian's open discussion about her past relationship challenges makes her current happiness with Cole feel earned and authentic to her audience.

Whitney Cummings’ Past Relationships: A Look Back

Before Chris Cole, Whitney Cummings had a few high-profile relationships that she often referenced in her comedy, using humor to navigate the complexities of modern dating.

The Miles Skinner Engagement

Cummings was previously engaged to Miles Skinner, a managing director at an advertising agency. He proposed in 2018 on her birthday while they were with her horse, King. However, the couple ultimately called off the wedding in 2020. Cummings was open about the reasons, citing her own issues with commitment and the pressure of marriage, which became a topical entity in her stand-up material.

Other Notable Relationships

Cummings has also been linked to other figures in the entertainment and sports worlds:

• Peter Berg: The comedian dated filmmaker, director, and actor Peter Berg, known for creating *Friday Night Lights*, from 2012 to 2013.
• Kerry Rhodes: She was also in a relationship with former NFL player Kerry Rhodes around 2014.

Her dating history reflects a search for a partner who could match her intelligence and drive, a quest that seems to have culminated in her deep connection with Chris Cole. The comedian's journey has been one of self-discovery, and her new engagement is a testament to finding a unique and fulfilling partnership.