Dear Prudence Uncensored: The Sister’s Breakup

Nicole Cliffe and Daniel Mallory Ortberg

May 23, 2019 6:01 AM

Help! My Sister’s Spectacular Breakup Is Destroying My Wedding.

Daniel Mallory Ortberg

May 23, 2019 6:00 AM

Help! My Dad Won’t Stand Up to My Homophobic Mom. Should I Invite Him to My Gay Wedding?

Daniel Mallory Ortberg

May 22, 2019 12:00 PM

Dear Prudence Podcast: Help! My Mother Disapproves of My Big, Expensive Wedding.

Daniel Mallory Ortberg

May 22, 2019 8:00 AM

Help! I Told a Joke So Bad It Cost Me All My Friends.

Daniel Mallory Ortberg

May 21, 2019 10:20 AM

Help! Should I Tell My Brother I Found the $20,000 He Hid in a Teddy Bear’s Butt?

Daniel Mallory Ortberg

May 20, 2019 3:42 PM

Help! Should I Dump My Girlfriend Over This One Disgusting Habit?

Daniel Mallory Ortberg

May 18, 2019 8:00 AM

Dear Prudence Uncensored: The Work Friend

Nicole Cliffe and Daniel Mallory Ortberg

May 16, 2019 6:01 AM

Help! My Children Are Furious I’m Having Sex With Their Half-Brother.

Daniel Mallory Ortberg

May 16, 2019 6:00 AM

Help! I Was Fat-Shamed on a Plane. Now I’m Afraid of Flying.

Daniel Mallory Ortberg

May 15, 2019 12:00 PM

Dear Prudence Podcast: Help! My Snobby Twin Thinks I’m Doing Life Wrong.

Daniel Mallory Ortberg

May 15, 2019 8:00 AM

Help! My Sister Writes Weird, Delusional Facebook Posts About My Baby.

Daniel Mallory Ortberg

May 14, 2019 6:00 AM

Help! Should I Tell My Dying Friend About Her Husband’s Creepy Sexts?

Daniel Mallory Ortberg

May 13, 2019 3:08 PM

Help! I Found Child Porn on My Fiancé’s Computer, but I’m Afraid to Report Him.

Daniel Mallory Ortberg

May 11, 2019 8:00 AM

Dear Prudence Uncensored: The Family Portrait

Nicole Cliffe and Daniel Mallory Ortberg

May 09, 2019 6:01 AM

Help! My Future Sister-in-Law Insists I Pay for Her Reception and Honeymoon

Daniel Mallory Ortberg

May 09, 2019 6:00 AM

Help! My Fiancé’s Cat Might Tear Our Family Apart.

Daniel Mallory Ortberg

May 08, 2019 1:04 PM

Dear Prudence Podcast: Help! How Do I Deal With a Racist—but Popular—Mom at My Kid’s School?

Daniel Mallory Ortberg

May 08, 2019 8:00 AM

Help! My Sister Doesn’t Think My Gay Daughter Deserves the Family Heirloom.

Daniel Mallory Ortberg

May 07, 2019 6:00 AM

Help! My Nephew Stole $4,000 From My Business. Now He Wants a Good Reference.

Daniel Mallory Ortberg

May 06, 2019 3:02 PM