edmontonscene’s first review of a podcast, but surely not the last!

Review by Vivian Poon

I believe that everyone should have a best friend to meet up with at least once a week and talk about literally anything, including their sex life!

For those who don’t have a BFF like that, listening to the podcast, Why Won’t You Date Me? is the next best thing because it simulates the experience of going out and gossiping with your girlfriend.

Nicole Byer — best known as the host of the Netflix Original, Nailed It! — is confused as to why she’s single because she’s funny, has a fat ass, and loves giving blow jobs.

Every Friday, Byer brings a guest onto her podcast and asks them why nobody will date her. Because Nicole is a comedian, many of her guests are also comedians. The show has other notable guests, such as Tess Holiday (a well-known plus-size advocate and model), Wes from Nailed It!, Jinkx Monsoon, and Bob the Drag Queen (Winners of Rupaul’s Drag Race Seasons five and eight, respectively).

I have been listening to a bunch of podcasts lately, especially during my study breaks. Thanks to COVID-19, all of my classes are online, so it helps to stop staring at a screen after a four-hour study session.

While on the hunt for comedy podcasts, I saw Why Won’t You Date Me? in the related section of a different podcast I was checking out. I noticed Byer’s name and was immediately interested. I am a huge fan of Nailed It!, so I knew I had to listen to at least one episode.

The first one with Will Hines exceeded my expectations, and before I knew it, I was listening to one episode after another.

Each episode starts with an opening song, which Byer sings loudly and slightly off-key. My favourite part is when she wails out, “PLEEEEASE TELL ME WHYYYYY” after singing “Why won’t you date me?” three times. Byer then introduces this week’s guest and asks something about them to let the audience get to know that person a little bit better. For example, she’ll ask what they’ve been up to, point out an interesting fact about them, where they’re from, what kind of dating apps they’re using, or their current relationship status.

Often, guests will ask Byer questions about her love life or bring up other topics to discuss. Sometimes, in the middle of the podcast, Byer will ask the guest to rate her Tinder and Bumble profile. Near the end, she will ask the guest if they would date her. If she has hooked up with the guest before, she will ask why they didn’t end up dating.

It’s priceless to listen to the guy stutter his way through an answer and try to be as nice as possible about it. Finally, the episode finishes off with Byer asking the listeners to rate the podcast and write a crude comment hitting on her in the comments section.

At the same time, some episodes delve into more than just romantic or sexual relationships. They examine other problems, such as dealing with difficult family members and the issues surrounding sex work.

In an episode with comedy writer Solomon Georgio, he talks about how his mother threw a fit in the middle of his brother’s wedding because she disapproved of him converting to Islam. She also refused to call her grandson by his name — even though he had the same name as Georgio’s brother — and called him by a different name for months.

Jiggly Caliente (from Rupaul’s Drag Race season four) discusses what it’s like to do sex work and what needs to change to make it safer. Caliente stated that sex workers are more likely to get STDs. Byer agreed and added that sex work needs to be decriminalized so that documents like paper trails can help sex workers avoid getting abducted or worse.

I love how Byer is willing to be open and confident enough to tell embarrassing or ridiculous stories about herself.

One of the guests on the show is a guy that she slept with once and she accidentally peed on his floor. During an episode with actor and director Dan Lippert, she goes into gruesome detail about sleeping with a man with a “literal broken” dick and how he “mushed it into a condom,” which ended up looking like “loose flesh in a balloon.” And then, he proceeded to mash it into her.

I especially like the inappropriate comments that Nicole reads out at the end of every episode. I think it’s a creative way to get listeners to interact with the show and gives an incentive to leave a review. Some of my personal favourites have been “I want to squeeze that puss and squeeze out those delicious margarita juices”, and “I want to stuff you like a build-a-bear.”

I have enjoyed almost all of the guests that Byer brings to the show. I appreciate that most of them are comedians who have worked with Nicole before, which makes each episode incredibly engaging to listen to. Each guest shares nuggets of wisdom and offers Byer advice, or sometimes, they’ll share their own funny hookup stories. It’s intriguing to hear about various experiences regarding relationships and one night stands, especially with guests who are in an open relationship or are, in their forties, attempting (and sometimes failing) to learn how to use dating apps.

Sadly though, Nicole rarely does profile ratings anymore, because she keeps forgetting to do them. In my opinion, this is a shame because the guests gave her great advice that the audience can probably use as well.

For example, Lippert offers advice on how Byer should organize her photos on Tinder. He explains how she should start with a normal picture first and leave her most outrageous picture (of her posing with bedroom eyes and a huge iridescent dildo) as the last one. A person who is interested enough to swipe through all of her photos might find it funny, and the photo will illustrate another side of Byer that the person can decide whether or not they like it.

He also states, “I think you want [a dating profile] to be like a Monet. Like, from a distance, this looks great. I’m not gonna let you see all of the splotches yet. Like, I’m going to give you a broader version of me. And through texting, you’ll learn a little bit more.”

Unfortunately, episodes that don’t centre around the theme of sex and relationships are less fun to listen to. For example, in the most recent Christmas episode with Georgio, he and Byer talked about random topics that popped into their heads, like healthcare, UK shipping, and airports. I found myself unable to pay attention, and I zoned out for the majority of that episode. I think if a show centres around a specific theme, it’s disappointing when an episode doesn’t give you what you’re expecting.

My favourite episode so far is the one with Bob the Drag Queen, because it’s thought-provoking to hear two Black perspectives on systemic racism and implicit bias.

Bob points out that “as Black people, imagine having every single thing you come up with, someone tells you it is unprofessional, it is ghetto. For example, what can we do with our hair? Dreadlocks. And they tell you, you can’t wear that to work, it’s unprofessional. Okay, how about braids? You can’t wear that, it’s unprofessional. How about a big afro? You can’t wear that because it’s unprofessional.”

My second favourite episode is the one with Lippert because it contains some of Byer’s funniest hookup stories. One of the ones she mentions is the time when she sleeps with a guy with a micro penis. She describes it as a “fleshy acorn sitting on two silver dollar pancakes,” and when he said he was going to have sex with her, she replied — in her head — “But with what??”

She also tried to suck it, but she said it was like having a thimble in her mouth. Other fun stories in that episode include what it was like for her to blow Lippert in a bathroom at a party and the time when she slept with a guy who did an awful Barack Obama impersonation. He almost threw up on her in the middle of having sex.

When listening to this podcast, I discovered a side of Byer that I never thought I would see. On Nailed It!, she is still silly and expressive, but professional. While I find her more reserved TV personality quite entertaining, I strongly prefer the crazier side she lets out on her podcast. I find Byer’s performance on her podcast refreshingly honest and hilarious. She’s not afraid to talk about whatever she wants, and she always does it in a lighthearted way.

Byer was born to do podcasts. She’s talkative, but also eloquent, expressive, and always has something interesting to say. She never seems to run out of hilarious and graphic stories to tell. I can also appreciate how she doesn’t take life too seriously and she’s always willing to laugh at herself. The warm and positive energy she brings every week never fails to make me smile and temporarily helps me forget that I’m in the middle of a worldwide pandemic.

Overall, I definitely recommend listening to Why Won’t You Date Me? as it gives an amusing commentary on the ups and downs of modern dating. Byer’s ability to transition between serious topics and scandalous stories often leads to an engaging and poignant experience. I’ve been enjoying it immensely so far, and I can’t wait to binge all of the other episodes that I haven’t had a chance to listen to yet!

The Why Don’t You Date Me? podcast is available on most of the major podcast sites