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5 Shocking Revelations About Whitney Cummings’ New Fiancé, Chris Cole (Updated 2025)

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The notoriously candid comedian, writer, and podcast host Whitney Cummings has a new man in her life, and the relationship status has officially leveled up. As of late 2024, the creator of hit shows like 2 Broke Girls and *Whitney* revealed she is engaged to professional skateboarder Chris Cole, a twist in her dating life that few saw coming. The news, which broke in November 2024, has completely changed the narrative around the comedian’s long-standing public cynicism about marriage, proving that even the most skeptical hearts can be won over by the right partner.

This article, fully updated for December 2025, dives deep into the identity of Whitney Cummings’ fiancé, Chris Cole, the details of their surprising proposal, and how this new chapter fits into the comedian’s complex and often hilarious history with love and relationships. From his legendary career in skateboarding to the couple’s seemingly unconventional pairing, we break down everything you need to know about the man who finally put a ring on it.

Whitney Cummings: A Complete Biographical Profile

Whitney Cummings is a powerhouse in the comedy world, known for her sharp wit, observational humor, and fearlessly tackling topics like sex, gender, and modern relationships. Her career spans stand-up, acting, writing, and producing, making her one of the most versatile figures in entertainment.

  • Full Name: Whitney Ann Cummings
  • Date of Birth: September 4, 1982
  • Age (as of Dec 2025): 43 years old
  • Place of Birth: Washington, District of Columbia, U.S.
  • Profession: Comedian, Actress, Writer, Producer, Director, Podcaster
  • Notable Works: Co-creator of the CBS sitcom *2 Broke Girls* (2011–2017), creator and star of the NBC sitcom *Whitney* (2011–2013).
  • Stand-up Specials: *Money Shot*, *I’m Your Girlfriend*, *Can I Touch It?*, and *Jokes*.
  • Podcast: Host of the popular podcast "Good for You" since 2019.
  • Education: Studied at the Annenberg School for Communication at the University of Pennsylvania, and later attended Boston University.

Cummings' work often draws heavily from her own life and experiences, including her struggles with codependency, anxiety, and a complicated relationship history. This vulnerability has made her a relatable figure for millions, leading to immense curiosity about her personal life, especially her romantic partners.

The Man Who Proposed: Who is Chris Cole?

The announcement that Whitney Cummings was dating, and subsequently engaged to, professional skateboarder Chris Cole sent a minor shockwave through her fanbase. Cole is not a typical Hollywood figure, but rather a legend in the world of street skateboarding, known for his technical skill and longevity in the sport.

1. Chris Cole is a Professional Skateboarder Legend

Chris Cole, born James Chris Cole on March 10, 1982, is a highly decorated American professional street skateboarder. He turned pro in 2000 and has built a career marked by numerous accolades, including being named Skater of the Year twice by *Thrasher Magazine* (in 2005 and 2009).

His impressive list of achievements includes winning gold medals at the X Games and being a dominant force in competitions like the Maloof Money Cup and the Battle at the Berrics.

2. They Have a Minimal Age Difference

Despite their different career paths, Whitney Cummings and Chris Cole are almost the exact same age. Cummings was born in September 1982, and Cole was born in March 1982, meaning they are both 43 years old as of late 2025.

This shared birth year likely contributes to their connection, providing a common ground of life experiences and cultural touchstones that transcends their professional differences. The comedian has often joked about the challenges of modern dating, making her relationship with a peer from an entirely different industry a refreshing change.

3. The Proposal Was Perfectly Low-Key and Unexpected

In a move that perfectly mirrors the couple’s low-key dynamic, Chris Cole proposed to Whitney Cummings during her daily hike in Topanga Canyon, right behind her Los Angeles home.

The comedian revealed the details on her podcast, "Good for You," sharing that the proposal was a complete surprise. The casual, intimate setting—far removed from a grand, public spectacle—was a fitting start to their engagement, especially for a celebrity who values privacy and authenticity over performative romance. This spontaneous moment, captured in a photo shared by outlets like TMZ, highlighted the genuine nature of their bond.

Whitney Cummings’ Evolving Views on Marriage and Past Relationships

The engagement to Chris Cole is particularly noteworthy because Whitney Cummings has historically been vocal about her skepticism toward traditional marriage. Her comedy specials and interviews frequently dissect the absurdity and expectations of modern relationships, often with a cynical edge.

4. She Was Previously Engaged to Miles Skinner

Before Chris Cole, Cummings was engaged to creative director Miles Skinner. Skinner proposed to her on her birthday in September 2018, surrounded by her beloved horses. However, the engagement was called off in 2020.

The experience with Skinner, which included a public engagement and a subsequent private breakup, deeply influenced her material on the complexities of commitment. She has spoken candidly about the pressure and the reality of navigating a serious relationship in the public eye. Other notable relationships in her past include dating emergency veterinarian Alex Barnes in late 2021, as well as rumored connections to former NFL player Kerry Rhodes and director Peter Berg.

5. The Engagement Signifies a Major Shift in Her Relationship Philosophy

Cummings has often discussed her evolving views on marriage and codependency on various podcasts, including "The Tim Ferriss Show." She admitted that her initial cynicism was rooted in personal experiences and observations, but that she was actively working to reframe her perspective.

Her relationship with Chris Cole seems to embody this shift. The focus appears to be less on societal expectations and more on genuine connection and mutual support. The fact that she is now planning a wedding—a concept she frequently mocked in her earlier stand-up—suggests a profound personal transformation. This new chapter is not just about finding a partner; it's about embracing vulnerability and redefining what a successful, healthy relationship looks like on her own terms.

The comedian's journey from a self-proclaimed "love addict" and cynic to an engaged woman is a powerful narrative that will undoubtedly provide fresh, hilarious material for her upcoming stand-up specials and podcast episodes. Fans are eagerly awaiting more details about the wedding and how her fiancé, Chris Cole, will feature in her future work.

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