Whitney Cummings' Boyfriend: A Dive Into The Comedian's Love Life

Prof. Melvina Ernser Jr. 08 Jun 2025

Introduction

Whitney Cummings, a celebrated American comedian, actress, and writer, has always been in the spotlight for her sharp wit and observational humor. Beyond her career, fans are equally curious about her personal life, especially her romantic relationships. In this article, we’ll explore Whitney Cummings' current boyfriend, her dating history, and how she balances love and career. Whether you're a fan of her comedy or simply intrigued by her relationships, this article will provide an in-depth look into her love life.

Who is Whitney Cummings Dating in 2025?

Chris Cole: The Latest Love

Currently, Whitney Cummings is in a relationship with Chris Cole, a professional skateboarder. This new romance has fans buzzing with excitement. Cummings revealed her new relationship during her "Touch Me" comedy tour, where she admitted that she's "ready to propose" to her younger boyfriend. The comedian's openness about her personal life during her performances has made her fans feel closer to her, creating a deeper connection with her audience.

How They Met

While Cummings hasn’t disclosed many details about how she met Chris Cole, it’s clear that their relationship is thriving. Fans are eager to learn more about this new chapter in Cummings' life, and she seems to be embracing the love and support from her fans.

A Look Back: Whitney Cummings' Dating History

Miles Skinner: The Former Fiancé

Before Chris Cole, Whitney Cummings was in a relationship with Miles Skinner, a creative director, and media strategist she met online in early 2017. After dating for over a year, the couple got engaged, and Cummings announced the exciting news in 2018. However, the engagement was called off, and the couple parted ways. Cummings discussed this period of her life during an interview on "Live with Kelly and Ryan," where she opened up about the challenges she faced during the breakup.

Alex Barnes: The Veterinarian

In 2021, Whitney Cummings made it "Instagram official" with her boyfriend, veterinarian Alex Barnes. The couple met while Cummings was dealing with a difficult situation, and she revealed how she met Barnes during her comedy tour. Although their relationship was well-received by fans, it eventually came to an end, paving the way for Cummings' current relationship with Chris Cole.

Rumored Hookups and Past Exes

Whitney Cummings' dating history includes a mix of high-profile relationships and lesser-known connections. While she hasn't disclosed all her past relationships, fans have speculated about various rumored hookups. However, Cummings prefers to keep certain aspects of her personal life private, focusing instead on her career and public appearances.

Whitney Cummings' Approach to Love and Relationships

Openness and Honesty

Whitney Cummings is known for her openness and honesty when it comes to discussing her personal life. During her comedy tours, she often shares stories about her relationships, making her fans feel more connected to her. This transparency has helped her build a loyal fan base who appreciate her authenticity and humor.

Balancing Love and Career

As a successful comedian, actress, and writer, Whitney Cummings has to balance her career with her personal life. Her ability to maintain this balance is a testament to her resilience and dedication to both her work and relationships. Fans admire her for her ability to juggle these aspects of her life while maintaining her signature sense of humor.

What Fans Love About Whitney Cummings' Relationships

Fans are stoked and super curious about Whitney Cummings' new romance with Chris Cole. They appreciate how Cummings shares her experiences with them, making her feel more relatable and down-to-earth. Here are some reasons why fans love Cummings' approach to love and relationships:

Her honesty about her personal life
Her ability to laugh at herself and her experiences
Her openness about dating and relationships
Her willingness to share her journey with her fans

Conclusion

In summary, Whitney Cummings' current boyfriend is Chris Cole, a professional skateboarder. Cummings has had a diverse dating history, including relationships with Miles Skinner and Alex Barnes. Throughout her personal life, Cummings has maintained her signature honesty and humor, making her a beloved figure in the entertainment industry. Fans appreciate her transparency and ability to balance her career with her relationships, creating a deeper connection with her audience. As Cummings continues to navigate love and life, her fans will undoubtedly remain supportive and curious about her next chapter.

Whitney Cummings' Boyfriend Miles Skinner

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