Comedian Nick Kroll (Big Mouth, Oh, Hello) joins Nicole for an episode of just... absolute chaos. They discuss how Nick asked his girlfriend to go steady, why playing a woman was his most challenging acting role, and using John Mulaney's hypnotist to quit

Comedian Sherry Cola (Joy Ride, Turning Red) shares her journey of coming out as bisexual, how she met her girlfriend, navigating dating in the queer community, and monetizing a breastmilk kink.WATCH this episode on YouTube at:https://youtu.be/RH4fK

Comedian Sarah Silverman sits down with Nicole to discuss meeting her boyfriend over Call of Duty, the challenges of dating as a female comic, and how many health studies are skewed against women. Plus, Nicole shares her experience getting hit on at Comic

We're back - and now in video form! Comedian and actress Lauren Lapkus (Newcomers podcast) joins Nicole to discuss why men lie about their heights, motherhood, and her recent trip to Victoria's Secret. Plus, they play a special game of F*ck, Marry, Kill:

In this best of episode, Emmy-award winning actressKeke Palmer(Nope, Lightyear)shares with Nicole how she got her first kiss from MySpace, why she avoids posting relationships on social media,and how she's learning to trust again after her boyfriend s

While we're on hiatus, we're bringing you the best of the podcast completely ad-free! In this episode, Nicoles close friendFrancesca Amber(host ofLaw of Attraction Changed my Life) opens up about the challenges of being a single mother to twins, the

In this iconic episode, Gabrus (High & Mighty), Nick Wiger and Mike Mitchell (Doughboys) join Nicole fresh off a power-hour to discuss how they would want to die, their favorite sex positions, and if they're into ass play. They also answer audience qu

While we're on hiatus, we're revisiting one of Nicole's favorite episodes! Comedian and actorPaul Scheer(The League,Black Monday) joins Nicole to chat about how his proposal toJune Diane Raphaelwent terribly wrong, how June's wedding ring was stolen

Were bringing you the best of Why Wont You Date Me?completely ad-free! In this episode, Nicole is joined by Skyler, who she met on Tinder. Things got awkward quickly when they realized they dated the same man. Nicole asks Skyler why she swiped right, w

As we continue our hiatus, we're bringing back some of Nicole's all-time favorite episodes! And oh boy, BUCKLE UP, because this one is WILD. Nicole is joined by drag queen Meatball and rapper Big Dipper, and things get crazy fast. They share a wild hookup