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Episode list
Why Won't You Date Me?
Seasons
Years
Unknown
Building Your Date's File (w/Larry Owens)
Thu, Nov 24, 2022
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How to Hack Into Your Partner's Phone (w/Keke Palmer)
Thu, Dec 1, 2022
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The First Black Chippendale Dancer (w/Quentin Plair)
Thu, Dec 8, 2022
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Let's Talk About The Bag Dress (w/LaLa Ri)
Thu, Dec 15, 2022
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Eloping on Christmas (w/Manila Luzon)
Thu, Dec 22, 2022
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Living Your Hoe Phase (w/Atsuko Okatsuka)
Thu, Dec 29, 2022
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Stories from Nicole's Road Dog (w/Christi Chiello)
Thu, Jan 5, 2023
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Pandemic Divorce (w/Punkie Johnson)
Thu, Jan 12, 2023
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The Sex Lives of Artists (w/Ilia Isorelýs Paulino)
Thu, Jan 19, 2023
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Nicole's Boyfriend Speaks His Truth (w/Dan Black)
Thu, Jan 26, 2023
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Celibate for 18 Years (w/Debra DiGiovanni)
Thu, Feb 2, 2023
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Having Sex On-Camera (w/Jordan Firstman)
Thu, Feb 9, 2023
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Dating a Groupie (w/Steph Tolev)
Thu, Feb 16, 2023
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Being The Only One Left (w/Michael Cruz Kayne)
Thu, Feb 23, 2023
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Marrying Your High School Sweetheart (w/Adam Pally)
Thu, Mar 2, 2023
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Mormon and Closeted (w/Bridger Winegar)
Thu, Mar 9, 2023
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Being 'In Like' vs Being 'In Love' (w/Gabrielle Dennis)
Thu, Mar 16, 2023
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Marrying for Tax Purposes (w/Jeff Hiller)
Thu, Mar 23, 2023
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Why Won't You Go Get a Transvaginal Ultrasound? (w/X Mayo)
Thu, Mar 30, 2023
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A Love Queen (w/Sasha Velour)
Thu, Apr 6, 2023
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Staying Friends with your Ex (w/James Marsden)
Thu, Apr 13, 2023
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"Don't Ask, Don't Tell" Poly Relationships (w/Zoe Lister-Jones)
Thu, Apr 20, 2023
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Lesbian Sex (w/Ashley Gavin)
Thu, Apr 27, 2023
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Secrets To a Long, Loving Marriage (w/John Leguizamo)
Thu, May 4, 2023
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Monogamously Challenged (w/Holly Robinson Peete)
Thu, May 11, 2023
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Hot Porn Seaches (w/Bridget Everett)
Thu, May 18, 2023
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Sugar Daddies (w/Sugar & Spice)
Thu, May 25, 2023
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Live Your Rom-Com Era (w/Sam Taggart)
Thu, Jun 1, 2023
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Transcending Norms (w/TS Madison)
Thu, Jun 8, 2023
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Fake It Til You Make It (w/Melvin Gregg)
Thu, Jun 15, 2023
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Finding Your Confidence (w/Jay Pharoah)
Thu, Jun 22, 2023
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Tasteful Dick Pics (w/Jermaine Fowler)
Thu, Jun 29, 2023
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Nicole Wins an Orgasm Contest (w/Matteo Lane)
Thu, Jul 6, 2023
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Catfishing Men on Craigslist (w/Bosco)
Thu, Jul 13, 2023
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Mutual Ghosting (w/Robin Fierce)
Wed, Jul 19, 2023
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Dating an Asexual (w/Gigi Goode)
Thu, Jul 27, 2023
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Gay Orgies (w/Jay Jurden)
Thu, Aug 3, 2023
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Romancing Overseas (w/Zurin Villanueva)
Thu, Aug 10, 2023
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300 Episodes of Why Won't You Date Me (w/Sasheer Zamata)
Thu, Aug 17, 2023
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Nicole Eats a Banana from a Sex Worker's Pussy (w/Naomi Rodgers)
Thu, Aug 24, 2023
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Feeling Safe in a Relationship (w/Uzo Aduba)
Thu, Aug 31, 2023
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Sex and Love Addict (w/Maria Bamford)
Thu, Sep 7, 2023
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Achieving 'Couple Goals' (w/Michael Jai White)
Thu, Sep 14, 2023
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Positive Affirmations to Change Your Psyche (w/Leslie Jones)
Thu, Sep 21, 2023
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Breaking Up (w/Eric Andre)
Thu, Sep 28, 2023
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Advice From an Intimacy Expert (w/Shan Boodram)
Thu, Oct 5, 2023
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Hurt People Hurt People (w/Kenny DeForest)
Thu, Oct 12, 2023
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Relationship Manipulation Tactics (w/E.R. Fightmaster)
Thu, Oct 19, 2023
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Kink Gone Wrong (w/Jonathan Van Ness)
Thu, Oct 26, 2023
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Saying I Love You (w/Ashley Blaine Featherson-Jenkins)
Thu, Nov 2, 2023
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28 more
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