Whitney Cummings' new boyfriend is professional skateboarder Chris Cole. Their relationship became public in August 2024, when Cummings commented on one of Cole's skateboarding clips on Instagram, saying, "There goes my babyyyy", to which Cole responded, "@whitneycummings [kiss emojis]."

After their Instagram reveal, the couple started appearing together at various public events, confirming their romance. Later, Cole shared a heartfelt birthday message for Cummings on September 4, 2024. He wrote on his Instagram stories:

It's my lady's birthday! What I tell anyone who says "omg I love her" is that you only know 10% of why you SHOULD love her. She is so much more magical than she even knows. SIMPLY THE BEST.

Cummings and Cole reportedly started dating in mid-2024 but kept their relationship private until August 2024.

James Chris "Cobra" Cole is a renowned American professional skateboarder known for his impressive skills and contributions to the sport. Born on March 10, 1982, in Statesville, North Carolina, Cole gained recognition for completing challenging tricks.

Some of his top tricks include the 360 flip, Switch Frontside flip, and Backside 360 ollie down the staircase at Wallenberg High School in San Francisco.

Chris was married to artist and tattoo enthusiast Christine Flannigan in 2007. They have two children: Wyatt Cole (son), born in 2006 and Penelope Cole (daughter).

Whitney has had a few notable relationships over the years, some of which have drawn public attention. Here's a look at her dating history and past engagements.

During the COVID-19 pandemic, Cummings met Alex Barnes, a veterinarian, while seeking help for her foster dog. They started dating in July 2021, and she even joked about wanting to propose to him. They went Instagram official in April 2021, captioning a hot tub selfie of them together.

Get you a man who will photo bomb your vain fear-driven selfies in the hot tub.

Whitney began dating Miles Skinner, a creative director, in 2017. During an appearance on Conan in November 2017, she revealed meeting her significant other online. Whitney Cummings and Miles Skinner kept their relationship relatively private until September 2018, when he proposed on her 36th birthday.

The engagement was a surprise, and Cummings shared the moment on social media, joking that she wished she had gotten a manicure beforehand.

Today I got engaged. I handled it great! This just goes to show that if you work on yourself, trust your gut, and keep your ego in check, you too can find love on a dating app.

However, in February 2020, Cummings announced that she had called off the engagement. She explained that wedding planning had become overwhelming, especially after her mother suffered a stroke. She emphasised that the breakup was amicable and free of drama.

I am not wearing an engagement ring. I am no longer engaged. Nothing nasty, no drama. I truly just was not ready to plan a wedding; the whole thing really overwhelmed me.

My mom is in bad shape health-wise. The idea of planning was just really overwhelming and kind of sad to me. I feel like planning a wedding should be fun and not a complete bummer.

Rumours circulated that Cummings briefly dated former NFL player Kerry Rhodes, though details about their relationship remain scarce.

Whitney dated filmmaker Peter Berg for about a year. She later described their breakup as one of the most painful experiences of her life.

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Whitney Cummings' boyfriend is professional skateboarder Chris Cole. She began dating him after calling off her engagement with Miles Skinner in February 2020. Their relationship became public in August 2024 when Cummings affectionately commented on one of Cole's skateboarding clips, confirming their romance.

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Source: TUKO.co.ke