Headgum, the leading comedy podcast network, has announced its acquisition of Why Won’t You Date Me?, the long-running, award-winning comedy and dating podcast hosted by comedian and actress Nicole Byer.
The podcast, which originally launched on the network in 2017, will return to Headgum as part of an expanded partnership that includes ad sales management through Gumball, Headgum’s marketplace for host-read ads. Additionally, Byer will begin recording video episodes from Headgum’s studios in Los Angeles and New York, adding a new visual element to the already popular show.
This announcement comes on the heels of Headgum’s recent signings of other high-profile podcasts, including Handsome, a comedy show from Tig Notaro, Fortune Feimster, and Mae Martin, and The Lamorning After from Emmy-winning actor Lamorne Morris. In September 2024, the network also launched Thanks Dad, a new podcast hosted by Saturday Night Live star Ego Nwodim. Together, these new acquisitions cement Headgum’s position as a dominant force in the comedy podcast space, known for nurturing both established and emerging talent.
Why Won’t You Date Me? has garnered a loyal fanbase over its eight-year run, thanks to Byer’s unique blend of humor and vulnerability. Each week, Byer invites fellow comedians, friends, and ex-flings to discuss the ups and downs of romance, from awkward first dates to outrageous hookup stories. The show has earned numerous accolades, including an iHeartRadio Podcast Award for Best Female Host, a Webby Award for Best Comedy Podcast, and an Ambie Award for Best Comedy Podcast. Its diverse roster of guests includes celebrities like Keke Palmer, Tony Hale, Nikki Glaser, Jesse Tyler Ferguson, Lil Rel Howery, and Franchesca Ramsey.
Byer is particularly excited about returning to Headgum, where she first launched Why Won’t You Date Me? in 2017. “It’s my favorite podcast child—just don’t tell the others,” she said. “I’m thrilled to bring her back home to Headgum. I’ve hosted WWYDM for many years, and it’s both terrifying and comforting to know there will always be new content in the world of dating—whether it’s fresh horror stories, new relationship scenarios, or unbelievably cute love stories. I’m excited to continue navigating it all with my listeners every week.”
Headgum’s Vice President of Content, Kaiti Moos, lauded Byer’s immense talent, saying, “There’s no question that Nicole is one of the top podcast hosts of all time. She is prolific, consistently hilarious, and Why Won’t You Date Me? is a comedy podcast classic. We’re beyond excited to reunite with her at this exciting stage of her career and our network’s growth.”
Marika Brownlee, Headgum’s Director of Marketing, added, “From iconic live shows to co-hosting Newcomers with Lauren Lapkus, Nicole has been an integral part of Headgum’s success. We’re honored to continue supporting her podcast empire and all the hard work she puts in.”
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Nicole Byer is one of comedy’s most versatile and successful voices. In addition to her podcasting success, Byer is the host of Netflix’s hit competition series Nailed It!, which earned her an Emmy nomination in 2020, making her the first Black woman to be nominated for “Outstanding Host for A Reality or Competition Program.” Byer was nominated for the award again in 2021 and 2022. She is also the host of Best Friends with Sasheer Zamata and 90 Day Bae with Marcy Jarreau, and co-hosts Newcomers with Lauren Lapkus. Byer’s debut solo stand-up special, Nicole Byer: Big Beautiful Weirdo, premiered on Netflix in 2023, and she can be seen in The American Society of Magical Negroes, which debuted at the 2024 Sundance Film Festival, as well as the upcoming film Thelma.
