Is Whitney Cummings Married? The Shocking Truth About Her Two Engagements And Current Fiancé, Chris Cole

The question of whether comedian and writer Whitney Cummings is married has been a persistent topic among fans, given her candid—and often hilarious—discussions about relationships on her podcast and stand-up specials. As of December 2025, the definitive and most current answer is no, Whitney Cummings is not married, but she is currently engaged to professional skateboarder Chris Cole. This news follows a history of high-profile relationships, including a previous broken engagement, which she has openly discussed, providing a fresh and unique perspective on modern dating and commitment.

The public's curiosity stems from her prominent career, where she has created successful sitcoms like *2 Broke Girls* and *Whitney*, and her brutally honest comedy style. Her personal life, particularly her journey toward marriage, has been a central theme in her work. The revelation of her engagement to Chris Cole, which she shared on her popular *Good For You* podcast, confirmed that the comedy powerhouse is officially off the market, even if she hasn't yet walked down the aisle.

Whitney Cummings: A Comprehensive Biography and Profile

Whitney Cummings is a multi-talented American comedian, actress, writer, producer, director, and podcaster who has become one of the most recognizable voices in modern stand-up comedy. Her work often focuses on gender dynamics, sex, and relationships, making her personal life a subject of intense public interest. Below is a detailed profile:

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• Full Name: Whitney Ann Cummings
• Date of Birth: September 4, 1982
• Place of Birth: Washington, District of Columbia, United States
• Age: 43 (as of December 2025)
• Education: University of Arizona (studying Film and Sociology), Annenberg School for Communication at the University of Pennsylvania (briefly)
• Career Highlights: Creator and star of the NBC sitcom *Whitney* (2011–2013); co-creator of the CBS sitcom *2 Broke Girls* (2011–2017); host of the popular podcast *Good For You*; released multiple stand-up specials including *I'm Your Girlfriend* and *Can I Touch It?*
• Notable Roles: Star of the film *The Female Brain* (which she also directed); appearances on *Chelsea Lately* and *Punk'd*.
• Current Status: Engaged to Chris Cole.

The Two Engagements: Miles Skinner vs. Chris Cole

While the search query "Whitney Cummings married" yields a negative answer, her journey to the altar has been a public and winding road involving two distinct engagements. Her transparency about these relationships provides insight into her evolving views on marriage and partnership.

The First Engagement: Miles Skinner

Whitney Cummings' first engagement was to veterinary technician Miles Skinner. The relationship began in 2018, and Skinner proposed to her on her 36th birthday. The proposal was a private, intimate affair, which she later confirmed on her podcast. However, the engagement was called off in 2020.

Cummings was open about the reasons for the split, emphasizing that there was "no drama" or "nasty" fallout. She explained that the decision was mutual and stemmed from a realization that they were better suited as friends. This candid discussion highlighted the modern reality that an engagement doesn't always lead to marriage, and that separating can be a healthy, adult decision, even when a diamond ring is involved. The relationship with Miles Skinner remains an important part of her dating history.

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The Current Engagement: Chris Cole

In a surprising and much-celebrated announcement, Whitney Cummings revealed in November 2023 that she was engaged once again, this time to professional skateboarder Chris Cole. Cole, a two-time *Thrasher Magazine* "Skater of the Year," is a legend in the world of professional skateboarding, known for his incredible skill and longevity in the sport.

The announcement came on an episode of her *Good For You* podcast, where she humorously admitted her surprise and difficulty in sharing the news. This engagement marks a new chapter in her personal life. The relationship with Chris Cole appears to be strong, with the couple sharing a connection rooted in their respective high-energy, demanding careers. Cole's background as a professional athlete, who has won numerous titles including the X Games, provides a unique contrast to Cummings' life in comedy.

Why the "Whitney Cummings Married" Search Persists

The continuous search for "Whitney Cummings married" is fueled by several factors, primarily her age, her public discussion of her desire for commitment, and her past high-profile relationships with figures like Kerry Rhodes and Peter Berg.

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• Her Comedy Material: A significant portion of Cummings' stand-up comedy and podcast discussions revolve around the pressures of dating, settling down, and the societal expectations placed on women to get married and have children. Her frequent exploration of these themes naturally leads the audience to constantly check her relationship status.
• The Sitcom *Whitney*: Her semi-autobiographical NBC sitcom, *Whitney*, centered on a couple navigating the complexities of a long-term relationship and the idea of marriage. This blurred the lines between her on-screen persona and her real life, causing confusion for casual viewers.
• The Recent Engagement: The most recent engagement to Chris Cole is still relatively new. The public is now eagerly anticipating news of a wedding date, leading to a surge in searches to see if the couple has secretly tied the knot. As of the current date, no wedding has been confirmed, and she remains his fiancée.

The Future of Whitney Cummings and Chris Cole

While Whitney Cummings has not yet become a wife, her current engagement to Chris Cole suggests that marriage is firmly on the horizon. The relationship appears to be a solid partnership, combining the worlds of high-level comedy and professional action sports. Entities like the *Good For You* podcast continue to serve as the primary source for fresh updates on their relationship, including any potential wedding plans or details about the custom engagement ring.

Fans are hopeful that this second engagement will lead to a successful trip down the aisle, finally putting the "is she married?" question to rest. For now, Whitney Cummings continues to focus on her thriving stand-up career, her work as a director and producer, and her role as a future wife, all while using her relationship experiences to generate some of the most insightful and hilarious comedy in the business.

In summary, Whitney Cummings is not married, but she is happily engaged to her fiancé, Chris Cole. This current relationship status is the latest, most important update in the comedian's love life, showing that even the most commitment-averse comedians can find their match.