Should I Date Someone Who Still Lives with Their Parents? feat. The Illustrious Blacks

Is It Weird To Send A Holiday Card As a Single Person? feat. Qween Jean

What Do You Do with Jealousy? feat. Tariq "Black Thought" Trotter

I Don’t Like My BFF’s Bae, Is It Possible to Get Along? feat. Dylan Marron

Is It Too Soon to Meet Them in Paris after Two Months of Dating? (Relatable!!!) feat. Norah Jones

How Do I Get Over Imposter Syndrome? feat. Julian Shapiro-Barnum

The Song That Got Away! feat. Vanessa Williams and Jillian Hervey

How Do I Tell My Parents I Want to Spend the Holidays Alone? feat. Sydnee Washington

To Hang Or Not To Hang My Partner’s Trash Art? feat. Raquel Willis

My New Boyfriend's Dog is Truly the WORST—Do I Breakup!? feat. Tasha Smith

You Can Talk About My Personal Life But Not My Private Life! feat. Nicole Bus

AN ASS THAT CAN SWALLOW YOU WHOLE AND OTHER WANTS AND WISHES feat. Danielle Sanchez-Witzel

How Do I Tell My Mom to Stop Flirting with My Friends?! feat. Georgia Hardstark

"Tickleball, Anyone?!" feat. Beth Stelling

Are Women Really That Great? (Yes!!) feat. Sasheer Zamata

Michelle & Jordan Talk Their Toxic Traits! feat. Dan Ahdoot

How Do I Tell My Parents I'm Not a Republican? feat. adrienne maree brown

Put Your Penis In Your Pocket Book feat. Ms. Pat

Once a Cheater, Always a Cheater? feat. Catherine Cohen

I Haven't Done "It" For a Whole Year... Am I Okay!? feat. Amber Ruffin