“Dying is easy, comedy is hard” is supposedly a death bed quote attributed to character actor Edmund Gwenn, who is most famous for playing Kris Kringle in the 1947 film Miracle on 34th Street.

Gwenn was absolutely correct in his observation and comedy podcasting is exhibit number one. Comedy and true-crime are two of the most popular genres in podcasting. Popularity breeds imitation and comedy podcasts proliferate in the podcasting space like Tribbles in the famous eponymously named Star Trek episode.

Comedy podcasts come in all shapes, sizes, and sounds. We have the “bros” who harken back to middle school with fart jokes and tales of their boogers. We have the edgy comics who think they push the envelope when, in reality, they’re just splashing around in crude observations that aren’t funny.

In summary, there are many more people in podcasting trying to be funny than are truly funny. Nicole Byer belongs to the category of “just plain funny.”

Nicole Byer is an actress, comedian, writer, author and podcaster, she is perhaps most well-known as the host of Netflix’s Emmy-nominated competition baking series Nailed It!

In 2020, Nicole made history by becoming the first black woman ever to be nominated in the category of “Outstanding Host for A Reality or Competition Program” and was nominated again in 2021 and 2022. Nicole can be seen in her debut solo stand-up special for Netflix, Nicole Byer: Big Beautiful Weirdo, and previously on the NBC comedy Grand Crew. Nicole can most recently be seen in Focus Feature’s The American Society of Magical Negroes, a satirical comedy and the 2024 American comedy film, Thelma. Both received rave reviews during their premieres at the 2024 Sundance Film Festival.

Why Won’t You Don’t Me is a comedy and relationship podcast hosted by Nicole Byer which debuted on December 1, 2017. The podcast features Byer and a guest exploring why she is single, while discussing topics related to love, life, and sex.

The format of an episode typically involves Byer introducing her guest/s, as they then talk about their respective experiences with sex, dating, relationships, and love. In most episodes, the guest will critique Byer’s online dating profiles, before closing the episode by discussing whether or not they would date her – and why.

While the featured guest is often another comedian, Byer has also hosted former partners, as well as her own childhood friends. Notable guests who have appeared on Why Won’t You Date Me? include Sasheer Zamata, Rachel Bloom, Jameela Jamil, Joel Kim Booster, Vicky Vox, and Trixie Mattel.

In 2019, Why Won’t You Date Me? won Outstanding Foreign Series at the Canadian Podcasting Awards, which is “awarded to a breakthrough show – across any format and category – produced outside of Canada.” In 2021, Why Won’t You Date Me? won the Best Overall Host – Female iHeartMedia Podcast Award. In 2023, it won best comedy podcast in the Ambies Awards.

The show recently announced that comedy podcast network Headgum has acquired the rights to the podcast. The acquisition comes on the heels of a recent announcement that the network also added Tig Notaro, Fortune Feimster, and Mae Martin’s podcast HANDSOME to its expanding lineup of comedy podcasts.

Headgum is a premier comedy podcast network behind shows such as Doughboys, Handsome, The Lamorning After, Gayotic with MUNA, and Seek Treatment with Cat & Pat.

As part of the deal, Nicole Byer will begin recording video episodes from Headgum’s LA and NYC studios. Headgum will also manage the show’s ad sales through Gumball, their marketplace for advertisers to buy host-read ads directly from podcasters.

The first Why Won’t You Date Me? episode under Headgum is out this week, and features an interview with comedian and personal friend of Byer, Lauren Lapkus (Orange Is the New Black, Crashing, The Big Bang Theory). Other upcoming guests include Randall Park, Sarah Silverman, Jimmy Kimmel, and Nick Kroll, among others. In each episode, Byer and fellow comedians, friends, and ex-flings talk romance and share their wildest dating tales, from cringeworthy first dates to jaw-dropping hookup stories.

“Nicole Byer says: “Why Won’t You Date Me? is my favorite podcast child – just don’t tell the others. I’m looking forward to bringing her back home to Headgum, where we first launched the show in 2017. I’ve hosted WWYDM for many years, and it’s scary and comforting to know that there will always be new content when it comes to dating – whether it’s fresh horror stories, new relationship scenarios, and unbelievably cute love stories – and I’m thrilled to be the host helping my listeners navigate it all every week.”

“There’s no question that Nicole is one of the top podcast hosts of all time – there is rarely someone who is so prolific and so consistently hilarious – and Why Won’t You Date Me? is a comedy podcast classic,” said Headgum VP of Content, Kaiti Moos.

New episodes of Why Won’t You Date Me? are released on Fridays and can be found wherever you listen to podcasts, including on the Why Won’t You Date Me? YouTube channel.