Whitney Cummings rocketed into the comedy spotlight with a fearless, anything-goes style that made her stand out from the start. Born in Washington, D.C.’s Georgetown neighborhood on September 4, 1982, Whitney has made her mark with a brand of stand-up that’s honest, sometimes uncomfortable, and always hilarious.
She put in years working the comedy circuit before breaking through to a bigger audience as co-creator and producer of the hit CBS sitcom 2 Broke Girls. Onstage, in specials, and behind the scenes, Whitney’s voice is distinctive: smart, sharply feminist, and never afraid to get candid about sex, relationships, or the weirdness of everyday life. Her comedy doesn’t just make people laugh; it nudges them to think about the world – and themselves – a little differently.
Whitney is also famous for speaking her mind – not just onstage, but everywhere. She openly discusses her struggles, her cosmetic surgery, and her bumpy love life, all of which frequently end up as material for her sets. If she bombs a joke or a relationship, she owns it and spins it into something worth sharing, never shying away from her own missteps.
Love Life and Relationships
Whitney’s dating history, much like her comedy, is authentic, occasionally messy, and full of self-awareness. These days, she seems to be single and has kept the details of her romantic life pretty private since her last engagement ended in 2020.
In her 2022 special, she cracked, “At this age, I’m not looking for red flags anymore – I’m looking for green flags. Just one man who returns a text within 24 hours and doesn’t have a secret family.” Classic Whitney: wry, candid, and getting to the essential absurdity of modern dating.
She’s had a few public relationships with familiar names in entertainment:
- Miles Skinner (2018–2020): Whitney got engaged to this creative director on her 36th birthday after about a year of dating. But wedding planning collided with her mother’s illness, and she decided to call it off. Announcing the split on her podcast, she said, “I’m not ready to plan a wedding,” true to her trademark honesty.
- Kerry Rhodes (2014): Her romance with the NFL player didn’t last long, but Whitney worked the experience into her act, joking about the disconnect between comedians’ and athletes’ lifestyles.
- Peter Berg (2012–2013): Whitney dated the director and producer for about a year. Even after the breakup, she’s spoken kindly of him, a testament to the maturity she’s brought to her relationships over time.
There have been rumors about other romances – people have speculated about her and fellow comedian Chris D’Elia because of their close friendship, but both have said they’re simply friends and colleagues. More recently, there was some buzz linking her to Alex Barnes, though neither confirmed a relationship.
She once told Jimmy Kimmel, “Dating as a comedian is weird because people expect you to be funny all the time. Sometimes I just want to eat my pasta in silence.” That line perfectly sums up her ability to find wit in even the awkward moments of her life.
What’s really striking about Whitney is how visible her personal growth has been. Early on, she often dated high-profile partners – people who looked good on paper. These days, she says she’s focused on deeper connection and real compatibility, not just status or convenience.
As she put it on her podcast: “I’d rather be alone than with someone who makes me feel alone.” That’s the kind of hard-won wisdom that resonates with fans who’ve stuck with her through her comedy evolutions – and her romantic ones.
Past Relationships
Miles Skinner
Kerry Rhodes
Peter Berg
Whether she’s riffing on dating disasters or letting down her guard, Whitney Cummings keeps connecting with people through that same unfiltered, laugh-out-loud honesty. She’s not afraid to tell the truth, and that’s what keeps us all coming back.