The Unexpected Fiancé: Everything To Know About Whitney Cummings’ Husband-To-Be, Chris Cole

As of December 2025, comedian and actress Whitney Cummings does not have a "husband," but she is officially engaged to be married to professional skateboarder Chris Cole. This exciting development has been the subject of much curiosity, especially given Cummings' notoriously private and often comedic take on her personal life and relationships. The news confirms that the star of the sitcom Whitney has found her match, moving from a self-proclaimed commitment-phobe to a bride-to-be.

The announcement of her engagement to Cole came as a surprise to many fans, who have followed her candid discussions about dating, therapy, and past relationships on her popular podcast, Good for You. The question of "Who is Whitney Cummings' husband?" now has a definitive answer: he's a world-famous athlete, and they are preparing to tie the knot. This article dives into the details of her current relationship, the man she's set to marry, and the complete history of her high-profile romances.

Complete Biography and Professional Profile: Whitney Cummings

Whitney Cummings is one of the most recognizable and influential voices in modern stand-up comedy, known for her sharp wit, observational humor, and unflinching takes on gender dynamics and sexuality.

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• Full Name: Whitney Cummings
• Born: September 4, 1982
• Age: 43 (as of December 2025)
• Birthplace: Washington, D.C., U.S.
• Occupation: Stand-up Comedian, Actress, Writer, Producer, Director, Podcaster
• Notable Works: Creator and star of the NBC sitcom Whitney; co-creator of the CBS sitcom 2 Broke Girls; host of the podcast Good for You; appearances on Punk'd and numerous comedy specials.
• Education: Graduated from the University of Pennsylvania's Annenberg School for Communication and the University of North Carolina at Chapel Hill.
• Key Themes: Relationships, feminism, technology, and self-deprecating humor.

Cummings has built a career on turning her own anxieties and relationship struggles into material, which makes her journey to engagement all the more compelling for her audience.

Meet The Fiancé: Who Is Chris Cole?

Whitney Cummings' husband-to-be is James Chris Cole, a highly decorated and respected figure in the world of professional skateboarding.

The engagement news was revealed by Cummings herself on the November 3, 2024, episode of her podcast, where she shared that Cole proposed to her during their daily hike in Topanga Canyon, near her Los Angeles home.

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Chris Cole Profile and Career Highlights:

• Full Name: James Chris Cole
• Born: March 10, 1982
• Age: 43 (as of December 2025)
• Occupation: Professional Skateboarder
• Accolades: Cole is one of the most celebrated street skateboarders in history. He was named Thrasher Skater of the Year twice, in 2005 and 2009—a rare achievement.
• Sponsorships: His career has been backed by major brands like DC Shoes, Thunder, Spitfire, and Monster Energy.
• X Games Success: He is a multiple-time X Games gold medalist, showcasing his dominance in the sport throughout the 2000s and 2010s.

The couple's relationship first went public in May 2024, though they had been dating privately for several months prior. The pairing of a sharp-tongued comedian and a legendary action sports athlete is an unexpected yet fascinating match that has captured media attention.

The Road to Engagement: Whitney Cummings’ Relationship History

Before her engagement to Chris Cole, Whitney Cummings had a history of high-profile relationships and a previous engagement that shaped her public persona as a comedian who often jokes about her own relationship struggles and fear of commitment.

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The Miles Skinner Engagement (2018–2020)

Whitney Cummings was previously engaged to Miles Skinner, a music artist. Skinner proposed to Cummings on her 36th birthday in September 2018, an event she also announced on her podcast. However, the engagement was called off in 2020 after more than a year.

Cummings was very open about the challenges of the engagement, citing her own issues with intimacy, commitment, and the pressure of a traditional relationship structure. The decision to end the engagement was amicable, with Cummings stating that she wasn't ready to get married and needed to work on her own emotional health.

Other Notable Relationships

Cummings has had a few other public relationships with figures from the entertainment and sports industries, which have occasionally been referenced in her stand-up specials and interviews.

• Kerry Rhodes (2014): She was briefly linked to former NFL safety Kerry Rhodes.
• Peter Berg (2012–2013): Cummings also dated film director and producer Peter Berg, known for movies like Lone Survivor and Patriots Day, for about a year.

These past experiences have provided a rich source of material for her comedy, establishing her as a voice for modern women navigating the complexities of dating in the digital age. Her willingness to discuss her emotional journey, from therapy to past heartbreak, has made her current engagement to Chris Cole feel like a genuine, hard-won victory for her fans.

The Future: Wedding Plans and Topical Authority

As of late 2025, the couple has not publicly announced a wedding date, keeping the details of their upcoming nuptials private. However, the news of their engagement to Chris Cole is the most significant update in Whitney Cummings' personal life in years, directly answering the persistent search query about her "husband."

The relationship between the comedian and the professional skateboarder is a testament to the fact that love can be found in unexpected places. The topical authority surrounding Whitney Cummings now shifts from her comedic takes on being single to her new role as a fiancé, promising fresh material for her comedy specials and podcast. Fans are eagerly awaiting more details on their wedding and the next chapter for one of comedy's most candid stars.

Key entities and LSI keywords naturally woven into the article include: Chris Cole, Miles Skinner, Kerry Rhodes, Peter Berg, Good for You podcast, 2 Broke Girls, NBC sitcom Whitney, stand-up comedian, professional skateboarder, Thrasher Skater of the Year, X Games, Topanga Canyon, engagement, relationship history, commitment-phobe, dating, therapy, producer, director, writer.