Relationships & Love

Dear Prudence | Advice on relationships, sex, work, family, and life

Slate

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Advice, commentary, and conversation from Daniel Mallory Ortberg, author of Slate's Dear Prudence column. Every week, Prudie and special guests answer questions about relationships, sex, work, family, and life.

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Dear Prudence: The Friend, Not Therapist" Edition

1:00:29 | Apr 16th

This week finds Dear Prudence live on stage at The Bell House in Brooklyn. Recorded on March 13th, 2019, Prudie was joined onstage by Jezebel writer, Jasmine Sanders.Together they dig into letters about what to do when the kids you nanny are beyond o...Show More

Dear Prudence: The "Sexual Side Effects" Edition

1:14:02 | Apr 9th

This week finds Dear Prudence live on stage at The Hamilton in Washington DC. Recorded on March 12th, 2019, Prudie was joined onstage by the host of NPR’s Pop Culture Happy Hour, Linda Holmes.Together they tackle letters about how to decide if you sh...Show More

Dear Prudence: The "Feeling Guilty" Edition

1:08:26 | Apr 2nd

This week finds Dear Prudence live on stage at the Brava Theater Center in San Francisco. Recorded on March 7th, 2019, Prudie was joined onstage by New York Times bestselling author Jasmine Guillory. Jasmine’s books include The Wedding Date, The Prop...Show More

Dear Prudence: The "Affair To Remember" Edition

1:09:35 | Mar 26th

This week finds Dear Prudence live on stage at The Soiled Dove Underground in Denver Colorado. Recorded on March 6th, 2019, Prudie was joined by writer Nicole Cliffe, who currently runs Slate’s Care and Feeding advice column, and was Daniel Ortberg’s...Show More

Dear Prudence: The "You Gonna Eat That?" Edition

1:11:41 | Mar 19th

Prudence is joined this week by writer Helen Rosner. She is the food correspondent for The New Yorker, and a former editor at places like Eater, Saveur, and New York Magazine.Together they tackle letters about what to do when a lonely neighbor treats...Show More

Dear Prudence: The “Good (Not Great) Sex” Edition

1:00:02 | Mar 12th

Prudence is joined this week by Sarah Shourd, a multi-media journalist based in Oakland, California. Her work combines fiction with rigorous journalism to elevate marginalized voices. She’s now working collaboratively on a graphic novel as a JSK Fell...Show More

Dear Prudence: The "Consent Agenda" Edition

47:19 | Mar 5th

Prudence is joined this week by writer and artist, John Leavitt, whose work has appeared in The New Yorker, Motherboard, Racked, And Marvel Comics.Together they tackle letters about what to do when your husband requests consent for any and all physic...Show More

Dear Prudence: The "Unrequited Colleague" Edition

47:32 | Feb 26th

Prudence is joined this week by Janet Cheatham Bell, who left her position as a textbook editor in 1984 to become a consultant to authors, the book publishing industry, and to produce her own books. She recently moved to the San Francisco Bay Area to...Show More

Dear Prudence: The "Praise Dog" Edition

54:05 | Feb 19th

Prudence is joined this week by Justine D'Souza, a social media community management professional who also works for a youth helpline. Outside of work, she enjoys performing in operas, plays, and musicals. Together they tackle letters about what to d...Show More

Dear Prudence: The "Don't Like Doodads" Edition

46:28 | Feb 12th

Prudence is joined this week by Favianna Rodriguez, an interdisciplinary artist, cultural organizer, and political activist based in Oakland, California. Her art addresses migration, economic inequality, gender justice, and ecology. She is also the E...Show More

Dear Prudence: The "Friendly Flakes" Edition

55:41 | Feb 5th

Prudence is joined this week by Martha Rynberg, an Oakland based writer and performer. She is the principal director of the Solo Performance Workshop, and is getting an online masters degree in how to keep cats from scratching on leather furniture.To...Show More

Dear Prudence: The "I'm Not Really Perfect" Edition

50:36 | Jan 29th

Prudence is joined this week by a close personal, if not a bit judgmental, friend, Maddie Chavez. Maddie’s judgements are known to be true of heart and strong of will.    Together they tackle letters about how to handle a boyfriend who thinks you’re ...Show More

Dear Prudence: The "Sell The Damn Ring" Edition

53:53 | Jan 22nd

Prudence is joined this week by writer and film critic Willow Maclay. Maclay runs the website Curtsies and Hand Grenades, and is co-author of the upcoming book Corpses, Fools and Monsters: An Examination of Transgender Cinema. Together they tackle le...Show More

Dear Prudence: The "Overloaded Friend" Edition

42:30 | Jan 15th

Prudence is joined this week by journalist and comedian Francesca Fiorentini. Fiorentini is a correspondent with Explorer on the National Geographic Channel and a regular guest on The Young Turks. She’s also the host and creator of The Bitchuation Ro...Show More

Dear Prudence: The "Always An Excuse" Edition

52:41 | Jan 8th

Prudence is joined this week by author and activist, Ebony Adams. Adams is the co-host of the podcast, Feminist Frequency Radio, along with Anita Sarkeesian and Carolyn Petit. She is also the co-author of the recently published History vs Women: The ...Show More

Dear Prudence: The "Up For Sitting Down" Edition

1:07:40 | Jan 1st

Facing an empty guest chair, Prudence grabs Phil Surkis, the producer of the Dear Prudence podcast, and takes him on a journey through Prudie’s past, revisiting a few of the memorable letters of 2018. Prudie and guests Anna Luberoff, Jess Reynolds, J...Show More

Dear Prudence: The "It's Already Weird" Edition

1:03:56 | Dec 25th, 2018

Prudence is joined this week by Julia Furlan, a Brooklyn-based journalist and podcast maker who is trying to learn how to hold a grudge. Together they take on letters about what to do when racist thoughts influence your choice of sperm donor, should ...Show More

Dear Prudence: The "Aren't We Friends?" Edition

56:49 | Dec 18th, 2018

Prudence is joined this week by writer Soraya McDonald, the culture critic for The Undefeated on ESPN. Previously, she wrote about pop culture for the Washington Post, focusing on issues surrounding race, gender, and sexuality. Together, they dig int...Show More

Dear Prudence: The "Addiction Fatigue" Edition

1:07:29 | Dec 11th, 2018

Prudence is joined this week by San Francisco writer Laura Turner, who also happens to be Prudie’s older sister. Together, they tackle letters about what actions to take when you’re friends with a married couple who abuse each other, what to do when ...Show More

Dear Prudence: The "Always Testing Me" Edition

1:00:01 | Dec 4th, 2018

Prudence is joined this week by Chris Randle, a New York based writer who came here from Canada. He's written for places like Hazlitt, The New York Times Magazine, Pitchfork, and Real Life.Together, they dig into letters about how to handle a brother...Show More

Dear Prudence: The "Socializing While Sober" Edition

59:56 | Nov 27th, 2018

Prudence is joined this week by Sophie Bee, a writer, speaker, nightlife promoter, and activist. She has written about film, music, queerness, and sex work. She is an organizer with Support Ho(s)e, a Chicago and New York City based collective advocat...Show More

Dear Prudence: The "Nixed Nuptials" Edition

1:01:28 | Nov 20th, 2018

Prudence is joined this week by Carta Monir, an Ignatz award-winning cartoonist living in Ann Arbor, Michigan, and Grace Lavery, an Assistant Professor of English at UC Berkeley.Together, this power trio tears into letters about what to do when your ...Show More

Dear Prudence: The "Animal Husband-ry" Edition

51:05 | Nov 13th, 2018

Prudence is joined this week by Jenée Desmond-Harris, an op-ed editor at the New York Times. One of the resolutions she's been working on all year is to become someone who inspires people say "you don't suffer fools". Together they tackle letters abo...Show More

Dear Prudence: The "Enough Is Enough" Edition

56:18 | Nov 6th, 2018

 Prudence is joined this week by Anna Sale, the host of the podcast, Death, Sex & Money, a show about the things we think about a lot and need to talk about more.Together they dig into letters about how to spend the holidays with a sister who is alar...Show More

Dear Prudence: The "Shy Spy" Edition

42:58 | Oct 30th, 2018

Prudence is joined this week by Hillary Eason and her brother, Tyler Eason. Hillary works in international development in Washington DC. Tyler is a data engineer in the Bay Area. They claim to have another sibling who is arguably better at giving adv...Show More

Dear Prudence: The “Misguided Text” Edition

40:50 | Oct 23rd, 2018

Prudence is joined this week by Tyler Mead, an associate producer of the queer comedy podcast, "Inside the Closet" hosted by comedians Emma Willmann and Matteo Lane. Together they dig into letters about what to do when the #metoo news has you not wan...Show More

Dear Prudence: The “Fun, Flirty Friends” Edition

46:43 | Oct 16th, 2018

Prudence is joined this week by Folu Akinkuotu, an internet person who lives in Boston. She’s an obsessive home baker who is always happy to share her baked goods from the endless supply in her purse. She has a better haircut than you and has never o...Show More

Dear Prudence: The “Brother Betrayal” Edition

52:46 | Oct 9th, 2018

Prudence is joined this week by Washington DC based writer, Zoë Selengut. Zoë works as a cataloger of rare and unusual books, ephemera, and other surprising cultural materials for Brian Cassidy Bookseller. Together they dig into letters about what to...Show More

Dear Prudence: The “Slightly Lesser Mess” Edition

57:20 | Oct 2nd, 2018

Prudence is joined this week by San Francisco based game critic, Carolyn Petit. Carolyn is the managing editor at Feminist Frequency, and a co-host on their podcast, Feminist Frequency Radio, alongside Anita Sarkeesian and Ebony Adams.Together they t...Show More

Dear Prudence: The "Obstinate Husbands" Edition

55:34 | Sep 25th, 2018

Prudence is joined this week by writer, actor and comedian Zahra Noorbakhsh. Zahra is co-host of the podcast #GoodMuslimBadMuslim, and The Pop Culture Collaborative has named her their Senior Fellow on Comedy for Social Change. Together they dig into...Show More

Dear Prudence: The “Unnecessary Shame” Edition

57:55 | Sep 18th, 2018

Prudence is joined this week by Assistant Professor of English at UC Berkeley, Grace Lavery. Her first book, “Quaint, Exquisite: Victorian Aesthetics And The Idea Of Japan,” is forthcoming with Princeton University Press in 2019, and she is currently...Show More

Dear Prudence: The "Sister Misery" Edition

55:26 | Sep 11th, 2018

Prudence is joined this week by Portland based author and technology expert Brook Shelley. Brook works for Turbine Labs and chairs the board for Basic Rights Oregon. Together they tackle letters about what to do when your stressed out sister’s only l...Show More

Dear Prudence: The "Done Raising Children" Edition

43:17 | Sep 4th, 2018

Prudence is joined this week by comedian Kate Willett, who has appeared on Comedy Central and Viceland. She has an album called Glass Gutter, and has a new special out on The Comedy Lineup on Netflix. Together they tackle letters about how to get out...Show More

Dear Prudence - The "Work Talk At Home" Edition

53:29 | Aug 28th, 2018

Prudence is joined this week by Jane McGonigal, the inventor of SuperBetter, a mobile game that has helped over a million people recover faster from depression and traumatic brain injury. Together they take on letters about what to do when you feel y...Show More

Dear Prudence: The "Leftover Food" Edition

43:39 | Aug 21st, 2018

Prudence is joined this week by Sorcha Reilly, an Oakland native who works in litigation consulting. She's preparing for her MBA at INSEAD, and has been known to procrastinate by playing top 40 hits on the violin. Together they tackle letters what to...Show More

Dear Prudence: The “Bare Minimum of Icy Neutrality” Edition

56:20 | Aug 14th, 2018

Prudence is joined this week by Kim Brinckerhoff, a lifelong Bay Area resident working on her master's degree in nursing and who does sexual assault advocacy in her free time (and also thinks everyone needs therapy). Together they tackle letters abou...Show More

Dear Prudence: The “Family Heirloom Accountant” Edition

49:32 | Aug 7th, 2018

Prudence is joined this week by writer and podcaster Colin Atrophy Hagendorf. Their memoir, Slice Harvester, is about eating a plain slice from every pizzeria in Manhattan, New York City history, and quitting drinking. They take on letters about what...Show More

Dear Prudence: The "Stoner Shame” Edition

49:48 | Jul 31st, 2018

Prudence is joined this week by writer John Thompson. Together they take on letters about how to talk to your parents about all your unpaid babysitting work, dealing with discomfort that your brother is dating a sex worker, how to avoid stoner shame,...Show More

Dear Prudence: The "Hots For My Cousin" Edition

51:10 | Jul 24th, 2018

Prudence is joined this week by writer, editor, and cool mom, Dominique Matti. Together, they tackle letters about how much you need to tell your work about your health problems, what do do about a casually racist coworker, should you involve your ch...Show More

Dear Prudence: The "Weapons Grade Pettiness" Edition

51:42 | Jul 17th, 2018

Prudence is joined this week by media critic Anita Sarkeesian. Together, they tackle letters about how to talk to your friends who aren’t receptive to your concerns that they may be co-opting your cultural and religious practices, what actions you ca...Show More

Dear Prudence: The “Invisible Girl” Edition

47:27 | Jul 10th, 2018

Prudence is joined this week by the Pulitzer Prize-winning author Jennifer Egan, whose latest book is Manhattan Beach. They take on letters that deal with what to expect from bosses when you have abusive co-workers, how to deal with the despair from ...Show More

Dear Prudence: The “Unexpected Inheritance” Edition

49:08 | Jul 3rd, 2018

Prudence is joined this week by marriage and family therapist Abigail Stone and Rebecca Ganetzky, a clinical geneticist. Together, they dig into questions about what do do when your ex husband tries to rename your daughter, should you conceal your ab...Show More

Prudence Presents: Better Life Lab

28:21 | Jul 1st, 2018

Today, we're coming to you with something special — the inaugural episode of Better Life Lab, the new podcast from Slate and New America. Better Life Lab looks at the challenges to work-life balance, and how we can change as a culture. Subscribe to B...Show More

Dear Prudence: The “Is Cheating Ever Ok?” Edition

1:01:54 | Jun 26th, 2018

Prudence is joined this week by Daniel Summers, a practicing pediatrician and regular contributing columnist to Slate’s Outward section, where he writes about health and medicine topics that affect the LGBTQ community. The Daniels take on questions a...Show More

Dear Prudence: The “Bullying Sister-in-Law” Edition

55:09 | Jun 19th, 2018

Prudence is joined this week by Talia Jane, a NYC-based aspiring comedy writer who makes smoothies for a living and who wants you to join a union. Daniel and Talia tackle questions about whether un-friending someone on social media because of their p...Show More

Dear Prudence: The "Demeaning My Coworkers" Edition

48:10 | Jun 12th, 2018

Prudence is joined this week by Gavia Baker-Whitelaw,  a geek culture critic at the Daily Dot, and co-host of the podcast Overinvested. This week they take on letters about how to talk to your child about transgender identity, how to talk to others a...Show More

Dear Prudence: The “Crush On My Job Interviewer” Edition

54:00 | Jun 5th, 2018

Prudence is joined this week by Courtney C.W. Guerra, an editor and writer who's been giving advice as Dear Businesslady since 2014. Together, they tackle questions about talking to your partner who thinks they know how to do your job better than you...Show More

Dear Prudence: The “Do I Buy the Ticket?” Edition

45:56 | May 29th, 2018

Prudence is joined this week by researcher and writer Jamie Fisher. Together they take on questions about whether or not to visit a close platonic friend that makes their partner jealous, how to talk to my partner about the fact that sex might be off...Show More

Dear Prudence: The “Poly Wedding Invite Etiquette” Edition

56:04 | May 22nd, 2018

Prudence is joined this week by writer and activist Jaclyn Friedman. Together they tackle questions about whether it’s ever ok to misgender someone when talking to a doctor, when to establish boundaries when working as a personal assistant, how to th...Show More

Dear Prudence: The “I Wanna Kidnap a Dog” Edition

39:23 | May 15th, 2018

Prudence is joined this week by standup comedian Myq Kaplan, who hosts the new podcast Broccoli and Ice Cream, and who is making his second appearance on the show. Together they take on questions about how to decide if your partner is being vulnerabl...Show More

Dear Prudence: The “Women Are Too Distracting” Edition

50:00 | May 8th, 2018

Prudence is joined this week by Jessie Lane, a social worker, mother, excellent cook, and holder of many opinions (and in this episode, holder of a baby). They tackle questions about how to deal with a coworker who tells the boss about their seemingl...Show More

Dear Prudence: The “Inspector Javert of Office Meatballs” Edition

50:57 | May 1st, 2018

Prudence is joined this week by Aria Velasquez, an audience engagement editor at Slate. First up, I’m worried my discussion with my eight year old about me and my husband’s sexual orientation has greatly confused her, please help! Next...my family is...Show More

Dear Prudence: The "Calculated Incursion On My Workplace" Edition

58:36 | Apr 24th, 2018

Prudence is joined this week by Kayla Whaley, a writer living outside Atlanta with a focus on disability, sexuality, and the body. First, this letter writer has a great job but is feeling anxious about her close friend applying for any available job ...Show More

Dear Prudence: The “Expensive Bulk Food-Grazer” Edition

47:00 | Apr 17th, 2018

Prudence is joined this week by Paola Dayanan, a TV-obsessed HR professional from Northern Virginia. First, a letter writer struggles with work after two devastating losses and a manager who doesn’t seem supportive. Next, a concerned letter writer ca...Show More

Dear Prudence: The "Mommy Moocher" Edition

47:40 | Apr 10th, 2018

Prudence is joined by Krystal Farmer: twitter, podcast, and emo music enthusiast. First, my partner will no longer accompany me to my family’s gathering because of the “redneck BS” he hears - what can I do? Next, my family won’t turn off their Alexa ...Show More

Dear Prudence: The “Wizard Privilege” Edition

42:08 | Apr 3rd, 2018

Prudence is joined by Margie Omero, a Democratic pollster and co-host of the bipartisan podcast “The Pollsters.” First up, my life feels unglamorous and the TV shows I watch just make me bitter, how can I address this? Next, I have a great relationsh...Show More

Dear Prudence: The “Falling for My Co-Parent” Edition

49:58 | Mar 27th, 2018

Prudence is joined by Baby Ange, host of the podcast Femme Too Deep. First up, a letter about “sex negativity” - this letter-writer did not enjoy sex with their partner but is having trouble finding constructive words to talk about it. Next, a father...Show More

Dear Prudence: The "Spousal Acknowledgement" Edition

40:01 | Mar 20th, 2018

Prudence is joined by Olga Kreimer, a journalist and grad student who writes an aggressively earnest advice column at the LA Review of Books. First up: will it be awkward if I don’t mention my husband in the acknowledgment of my first book since he w...Show More

Dear Prudence: The “Holidays of Their Own Design” Edition

42:07 | Mar 13th, 2018

Prudence is joined by Josh Gondelman, stand up comedian and writer for Last Week Tonight with John Oliver. First up, my Uncle says he won’t come to my wedding unless he’s joined by the woman he had an affair with, but my Aunt and their kids are still...Show More

Dear Prudence: The "Early Summer Chicken" Edition

47:19 | Mar 6th, 2018

Prudence is joined by powerhouse couple Gillian Evans and Lucy Mueller to help answer letters. First up: I’ve begun fostering a young child whose parents want me to prepare halal meals for him, but my family’s diet is much different - what should I d...Show More

Dear Prudence: The “Nosey Desk-Searching Boss” Edition

47:58 | Feb 27th, 2018

Prudence is joined by Justine D’Souza, a Phone Support Counselor for a youth helpline. We start with a job seeker who has concerns about disclosing their health problems during the interview process. Then, an employee whose boss searches their desk a...Show More

Dear Prudence: The “Relentlessly Friendly Neighbor” Edition

47:50 | Feb 20th, 2018

Prudence is joined by Jolie Kerr, a cleaning expert, advice columnist and host of the podcast, Ask a Clean Person. We begin with a concerned letter-writer whose sister is involved with a reckless and dangerous partner on how she can remain supportive...Show More

Dear Prudence: The “Not Your Mom” Edition

48:52 | Feb 13th, 2018

Prudence is joined by writer and self-appointed mom friend Jess Reynolds. First up, my ex and I “split the sheets” (tamer than you might think) after our career paths didn’t align, but I’m feeling drawn to him again even though I’m engaged to someone...Show More

Dear Prudence: The “Not Unconditional Love” Edition

54:15 | Feb 6th, 2018

Prudence is joined by hosts of the podcast By the Book: Kristen Meinzer and Jolenta Greenberg. First, how can I talk to my parents about feeling like I’m only acknowledged for academic achievements? Next, advice for an older sister unsure of how to h...Show More

Dear Prudence: The Live “Cruise-ship Romance” Edition

1:08:12 | Jan 30th, 2018

Our first live show! Prudence is joined onstage at the Brava Theater in San Francisco by writer and advice columnist Nicole Cliffe and lawyer and novelist Jasmine Guillory who read through letters and answer questions from the crowd. The team helps a...Show More

Dear Prudence: The “Tepidly Panromantic” Edition

45:22 | Jan 23rd, 2018

This week, writer Rohin Guha tells us of the joys of leaving Twitter post Trump election. First, the Prudence team takes on gender discrimination at a so-called forward-thinking progressive company. “Tired Asexual” asks “how do I regain my ability to...Show More

Dear Prudence: The “Ongoing Fling with a Famous Person” Edition

57:24 | Jan 16th, 2018

Prudence is joined this week by Charlotte Shane, author, essayist, and co-founder of TigerBee Press. First up - what to say when your sister compares your desire to have a child with adopting a cat. And how can I respectfully deal with attending frie...Show More

Dear Prudence: The “Reverse Kids Get Off My Lawn” Edition

46:51 | Jan 9th, 2018

This week we tackle the timeless question of how to eat from a jar of peanut butter in public when you don’t have a utensil. Then, farmer, educator, and food justice advocate Anna Luberoff joins to help with the mailbag. First, when dealing with over...Show More

Dear Prudence: The "Eternally Engaged" Edition

46:05 | Jan 2nd, 2018

This week we’re revisiting some of the trickiest, thorniest questions of the past year. First up: I’ve been engaged for five years with no wedding in sight. Help! What do I say to strangers who tell me I’m “not dark enough” to be from my home country...Show More

Dear Prudence: The "Personal ATM" Edition

49:33 | Dec 26th, 2017

This week we’re revisiting some of the trickiest, thorniest questions of the past year. First up: I keep lending my friend money and she never pays me back. Help! Then: I love my daughter-in-law, so why doesn’t my son want me talking to her? My emplo...Show More

Dear Prudence: The "Selfish Sister" Edition

55:33 | Dec 19th, 2017

We’re kicking off this week with some listener feedback on good problem to have – adjusting to earning enough money for more than just the essentials of life! And then, professional trans lesbian Elizabeth Mills joins to respond to your letters! Firs...Show More

Dear Prudence: The "Schrödinger's Stolen Cat" Edition

52:38 | Dec 12th, 2017

First up: An enthusiastic endorsement from Prudence for walking out of movies you don’t like! Then, academic and pop culture writer Anthony Oliveira joins to tackle your letters: How do I get my husband to stop using a body spray that makes me ill? M...Show More

Dear Prudence: The “Dirty Secret” Edition

48:25 | Dec 5th, 2017

Advice enthusiast and diversity consultant Valerie Aurora joins for a discussion of keeping your Christmas costumes away from Thanksgiving. Then onto your letters! First up: My best friends are growing closer and leaving me behind. Help! Should I tel...Show More

Dear Prudence: The “Oh, Roger” Edition

50:50 | Nov 28th, 2017

Listener Rachel Tibbetts joins for a doozy of a batch of sibling and family related letters. First up: my sister is repeating the same mistakes as my homewrecker father and she expects my support. Help! My parents never gave me a dime growing up and ...Show More

Dear Prudence: The “Master of Disaster” Edition

42:26 | Nov 21st, 2017

Dear Prudence is back with her annual reminder: it’s okay to ruin the holidays! Then, advice columnist Anna Pulley joins to respond to your letters! First up: can an open marriage save my sexless one? I moved to a retirement community where 1970s-sty...Show More

Dear Prudence: The “Drama Tornado” Edition

1:00:59 | Nov 14th, 2017

Author Sarah Gailey joins Prudence to advise on matters of laundry, sisterhood, salary, and more! First up: what’s the protocol for abandoned clothes in a public dryer? Then: Should I tell my sister I think marrying her fiance is a mistake? My friend...Show More

Dear Prudence: The “Wishin’ Boot” Edition

52:16 | Nov 7th, 2017

Prudence is back to tackle your letters! First up: I think my workplace is about to hire the terrible boss from my last job. Help! The love of my life left me for a friend of ours when I was pregnant with his child – am I supposed to try to co-parent...Show More

Dear Prudence: The “Friend of the Devil” Edition

39:13 | Oct 31st, 2017

Writer Rachael Herron joins Prudence to tackle a bundle of tricky letters! First up: Should I have said something to the men making sexist comments within earshot of my wife? My friend ignored my warnings about her terrible ex – now she says I abando...Show More

Dear Prudence: The “Go Dutch” Edition

45:38 | Oct 24th, 2017

Writer and Bitch magazine co-founder Lisa Jervis joins Prudence to hash out how to be the best “mysterious widow” – and respond to your letters! First up: Should I tell an acquaintance her boyfriend is a known rapist? My sister’s fertility battle is ...Show More

Dear Prudence: The “Rich Girl” Edition

54:28 | Oct 17th, 2017

Dear Prudence and guest Mary Goss navigate your family and relationship quandaries. First up: Is it selfish to feel fear after surviving tragedy when other people had it way worse? How can I get my hearing family to accept me? My adoptive sibling doe...Show More

Dear Prudence: The “On the Nose" Edition

52:17 | Oct 10th, 2017

In a spirit of excitement and terror, Prudie and Washington Post writer Amanda Erickson, jump into your letters. First up: I punched an emotionally abusive family member in the face – how do I make it up to her? How do I get my in-laws to stop callin...Show More

Dear Prudence: The “Good Grief" Edition

54:17 | Oct 3rd, 2017

Y.A. fiction writer and advocate for the disabled Maggie Faid joins Prudie to consult on matters of wedding guests, grief, and giving iPads to strangers. Should I tell my best friend how sad I am that she can’t come to my wedding? My sister tells eve...Show More

Dear Prudence: The "Hot Mess" Edition

56:32 | Sep 26th, 2017

Former Toast editor Nikki Chung joins Prudie to tackle a thorny bunch of your letters! First up: I’m living with a slob and I can’t afford to move out. Help! How do I get my husband to be kinkier in the bedroom? I might have prompted my daughter to m...Show More

Dear Prudence: The "Sunk Cost" Edition

49:51 | Sep 19th, 2017

Writer and commentator Lindy West joins Prudence to encourage Thelma-and-Louise-style road trips for jilted lovers and discourage kicking people out of wedding parties. First up in your letters: My boyfriend period shames me. Help! My fiancé has been...Show More

Dear Prudence: The "Rumpelstiltskin" Edition

53:39 | Sep 12th, 2017

Today on Dear Prudence: baby-stealing, stalking, and insufficient wokeness. First up: My boss keeps joking about wanting to take my baby. Help! Should I tell potential employers I had a stalker? My husband’s kids found out he smokes weed and he’s bla...Show More

Dear Prudence: The "Checking In" Edition

58:04 | Sep 5th, 2017

Buzzfeed's Nichole Perkins joins to help out with your letters! I was open about my depression on social media and only some of my friends reached out to me – should I stay close with the others? The woman who ruined my marriage got hit by a car... a...Show More

Dear Prudence: The "Pray on This" Edition

54:59 | Aug 29th, 2017

First up: an exciting update on the one true way to date a former boss and how Prudie helped make it happen. Then, your letters! My mom wants me to discourage my daughter from doing “boy” things. My friends are convinced my boyfriend is a stalker! My...Show More

Dear Prudence: The "Strangers on a Train" Edition

54:50 | Aug 22nd, 2017

Today, it’s a coming out party for first-time fig-eaters, brothers, people who don’t want to talk about their hair, artists, and more! First up: My dad wants my brother to wait to tell my conservative grandma he’s gay, but I think he should come out ...Show More

Dear Prudence: The "Feelings Roulette" Edition

48:00 | Aug 15th, 2017

Today we’ve got a very important update regarding the bidet letter! Then, Ali St. James & Olivia Pourzia join Prudie to triple-team your problems. My parents are insisting on helping me furnish my grad school apartment, but keep hinting that it’s a f...Show More

Dear Prudence: The "Panoply of Deviance” Edition

46:27 | Aug 8th, 2017

Writer, commentator and professor Roxane Gay joins Prudie to tackle your problems with online dating, bosses, exes, kids, and more! How do I avoid matching with my students on online dating apps? My boss won’t stop telling me to smile. Help! Should I...Show More

Dear Prudence: The "Mulligan" Edition

43:59 | Aug 1st, 2017

Prudence is joined by guest Alyssa Furukawa to get real about what it means to say “I’m on my way.” Then, onto your letters! I’m a pansexual woman married to a cis man – should I still come out to my homophobic family? My in-laws won’t accept my disa...Show More

Dear Prudence: The "Radical Unfriendliness" Edition

51:26 | Jul 25th, 2017

Dear Prudence is joined by BuzzFeed’s Bim Adewunmi to respond to your letters. First up: how do I handle people who tell me I’m not brown enough to be Indian? Then, romance issues: my best friend can’t get over my fiancé’s past and won’t come to our ...Show More

Dear Prudence: The "Open it Up" Edition

35:35 | Jul 18th, 2017

Matt Albrecht and Hannah Malyn of the podcast “Matt and Hannah Know it All” join Prudie to advise on your inquiries. First up: I know I should end my friend-with-benefits relationship, but I don’t want to. How do I cut ties with an emotionally abusiv...Show More

Dear Prudence: The "Bidet and Boujee" Edition

42:43 | Jul 11th, 2017

First up: is a movie franchise trying to gaslight Prudie? Then, onto your letters: I’m a think I’m a pretty progressive mom, but I don’t understand the gender fluidity movement. I asked my friend not to drink with my alcoholic parents and she turned ...Show More

Dear Prudence: The “Flowers in the Attic” Edition

48:37 | Jul 4th, 2017

First up: how Prudie and her ex, Jamie Shuler, bonded over Flowers in the Attic. Then, the two tag team your letters, starting with a workplace matter of misplaced credit. Then, onto sibling strife: My sister lied about her dog dying – should I confr...Show More

Dear Prudence: The “Capitalism is the Problem” Edition

44:22 | Jun 27th, 2017

Writer and journalist Laurie Penny joins Prudence today to tackle your family and work quandaries! How can I convince my husband to buck social pressure and stick to being a stay-at-home dad? My apartment building reeks of pot and makes me nauseated ...Show More

Dear Prudence: The “Dealbreaker” Edition

47:55 | Jun 20th, 2017

Comedian Myq Kaplan joins Prudence for a heated conversation about stoves. Then, onto your letters: Is meat a good enough reason to end a relationship? Should I fight for more money to close the gender wage gap even though I’m fairly paid? My son won...Show More

Dear Prudence: The “Call 311” Edition

41:26 | Jun 13th, 2017

First up, an opening statement from Prudence on the merits of 3D BC movies. Then, your letters! When is it okay to ask for exclusivity in a relationship? Can I cut down my reclusive neighbor’s dead tree? I’m trying to get back into the dating world, ...Show More

Dear Prudence: The “Workplace Hazard” Edition

51:13 | Jun 6th, 2017

Prudie’s brother-in-law Zack Turner joins to advise on your family, workplace and relationship dilemmas! First up: How can I get my mom to stop shaming me for gaining weight my first year at college? Then: my introvert boyfriend refuses to socialize ...Show More

Dear Prudence: The “Resignation” Edition

53:58 | May 30th, 2017

Prudence is joined by novelist Esmé Weijun Wang to advise on a batch of your family and relationship issues. First up: I fell in love with my dead husband’s best friend – then my in-laws found out and all hell broke loose. Help! When’s the right time...Show More

Dear Prudence: The “Death of the Ego” Edition

50:25 | May 23rd, 2017

Prudie learns about birthday spankings this week! Plus, how smartphones ruined pushing your friends into pools. Then, your letters! Should I report the employee who creeped me out at an internship I no longer have? How do I let my friends and family ...Show More

Dear Prudence: The “Cat-astrophe” Edition

47:51 | May 16th, 2017

Prudie and guest Ben Gullard get real about handling criticism. Then they tackle your letters! First up, a new take on cat conundrums: My wife thinks I love our cat more than her and I think she may be right! I’m upset that my husband doesn’t want my...Show More

Dear Prudence: The “Gravity Is Mad at You” Edition

43:41 | May 9th, 2017

Prudie kicks it off on a light note this week: we’re all going to die someday and the sky is scary. Then, onto your letters! My love worries that I’ll be giving up too much if we move across the country so he can take a rare opportunity. My husband r...Show More

Dear Prudence: The “United Front” Edition

43:05 | May 2nd, 2017

First off, Prudie’s open door policy: open doors for people when it makes sense. Then onto your questions: My MIL is telling my nine-year-old to give up on school because she’ll be a stay-at-home mom one day. My wife says she supports my transition, ...Show More

Dear Prudence: The "Hardly Working" Edition

58:49 | Apr 25th, 2017

First, a plug for more rivalries to be battled out through the giving of jewels. Then, Prudence is joined by gem Ashley C. Ford to answer your questions! I got stuck with the dramatic girl in my night class to work on a group project – how do I handl...Show More

Dear Prudence: The “Dickensian” Edition

48:16 | Apr 18th, 2017

Prudence is joined by award-winning Bay Area writer Charlie Jane Anders to give award-winning advice. First up: my sister remembers a completely different childhood than me and it’s driving a wedge in our relationship. Then, some parental problems: M...Show More

Dear Prudence: The “Anti-Pronoun” Edition

48:47 | Apr 11th, 2017

Prudie says, nine times out of ten it is not a good idea to steal someone else’s pet. Then, your questions: My husband refuses to do anything about his snoring and it’s keeping my family up at night. My friend overcharged me for rent and lied about i...Show More

Dear Prudence: The “Raise the Bar” Edition Part 2

33:22 | Apr 4th, 2017

Jos Lavery is back to help with more of your questions! First, two very different letters about depression: my husband has disengaged from our marriage; a friend I’m not very close to anymore is using me as his only emotional outlet. Then, I like my ...Show More

Dear Prudence: The “Raise the Bar” Edition Part 1

39:21 | Mar 28th, 2017

Prudence is joined by writer and academic Jos Lavery to answer your questions! First, my adult child just came out as trans – I support her, but when do we get to start talking about things other than being trans? A guy in my dorm sets an obnoxious a...Show More

Dear Prudence: The “Voyagers” Edition

42:04 | Mar 21st, 2017

First up: A beginners guide to Star Trek. Then, onto your questions: Should I stay with my narcissistic husband to protect my kids from him? Was I wrong not to tip a masseuse that overcharged me? Is it inappropriate for me to go to the funeral for my...Show More

Dear Prudence: The “P.S.A.” Edition

44:58 | Mar 14th, 2017

A request from Prudence: be the kind of Starfleet that you wish to see in the world. Then, onto your questions with awkward situation pro Emily McDowell. My friend surprised me by covering my hotel room for her wedding – do I need to up the ante on t...Show More

Dear Prudence: The “Dolly Dearest” Edition

38:28 | Mar 8th, 2017

Objectively, the worst thing that can happen is getting a thumbs down while driving. Prudence is joined today by writer Jasmine Sanders to advise a woman who’s worried her husband wants to adopt a child and she doesn’t. Then: how to act if you secret...Show More

Dear Prudence: The “Workplace Politics” Edition

32:22 | Feb 28th, 2017

Prudie is joined by herself on a very special solo episode of Dear Prudence. First up, a listener voicemail: My partner is worried our role playing is bad for me, but I don’t think it is. Then onto your letters! Then onto your letters! Will strangers...Show More

Dear Prudence: The “Cats Can Be Gay” Edition

41:57 | Feb 21st, 2017

If you don’t like it when people say “no problem,” then you’re the one with the problem, Prudie says. Then onto your questions: How do I talk to my adopted black daughter about race? My husband won’t keep his hands off me in public! I’m gay – what ne...Show More

Dear Prudence: The “Oppression Olympics” Edition

56:48 | Feb 14th, 2017

Feeling hopeless about the state of the world? Prudence has some advice for how to carry on without totally losing it. Then, writer Shafiqah Hudson joins Prudie to answer your questions: How do I convince my friend that he benefits from white privile...Show More

Dear Prudence: The “Line in the Sand” Edition

49:03 | Feb 8th, 2017

First off, some cold hard truth from Prudence: it never works to have a chore wheel. Then, onto your questions. Should I confront an acquaintance if I think he may be cutting himself? Then, my boyfriend’s business partner is a horrible house guest an...Show More

Dear Prudence: The “Chasing Amy” Edition

43:39 | Jan 31st, 2017

A friendly reminder from Prudence: advice is not one-size-fits-all! Writer and podcaster Christina Grace joins Prudie to help a woman break it to her in-laws that her family won’t be going to church; a military mom decide who should care for her daug...Show More

Dear Prudence: The “Young Guns” Edition

42:21 | Jan 24th, 2017

Prudie says it’s okay to ghost your social media followers, but not a child who thinks you’re her family. Then, MTV writer Jane Coaston joins in to advise on what to do if your mom uses surviving cancer as an excuse to spoil your kids. How to tell a ...Show More

Dear Prudence: The “Giving Tree” Edition

43:44 | Jan 17th, 2017

Prudie puts in a plug for queries about good fortune only. Then, she and writer Caille Millner tackle more serious problems: I’m convinced my husband had an affair with his boss, but he denies it. My mom is terrible with money. How can I get her to s...Show More

Dear Prudence: The “Family Matters” Edition

36:34 | Jan 10th, 2017

Prudie and guest Juan-Pablo Brammer explore the fine line of low-key racism. Then, your questions: How can I keep my sister from terrorizing my new boyfriend? Can I tell my husband’s parents not to hook up in my kid’s bed? How do I tell my husband I’...Show More

Dear Prudence: The “Insomnia” Edition

39:22 | Jan 3rd, 2017

I lent a family heirloom to a friend and she’s going to burn it in honor of her deceased child – can I ask for it back? “Nope!” says Prudence. Then your questions: Can I delay my breakup for financial gain? My partner won’t stop waking me up for triv...Show More

Dear Prudence: The "Rocky II" Edition

46:16 | Dec 27th, 2016

Rocky returns! The aspiring poker player writes back to make the case for quitting his day job (and if this makes no sense, check out the 11/29 “Anger Management” show). We’re rooting for you, man. Then, Mallory and comedian Avery Edison tackle your ...Show More

Dear Prudence: The "Timing Is Everything" Edition

42:50 | Dec 20th, 2016

Mallory and guest Andrea Silenzi of Slate podcast “Why Oh Why” take on big issues, starting with the weighty question of how long you should wait to move on when someone you’re dating goes missing at sea. Then to your letters: I was ready to forgive ...Show More

Dear Prudence: The “Death, Sex & Money” Edition

36:16 | Dec 13th, 2016

A soon-to-be bride wants to buck a patriarchal wedding tradition. A wife wants her husband to buck up and tell his father he can’t come over every weekend. A man wants to leave a longterm relationship, but he’ll leave his partner without any bucks. M...Show More

Dear Prudence: Live!

1:06:01 | Dec 6th, 2016

Mallory and guest Samantha Powell come to you live from the Now Hear This festival in LA. And a warning: things get rowdy! An American man wonders if he can divorce his non-English-speaking wife … because he’s bored explaining things to her. Then, th...Show More

Dear Prudence: The "Anger Management" Edition

47:27 | Nov 29th, 2016

Mallory’s dad v. William Shatner. Then your questions: first, how do I relate to a dad who was absent and abusive while I was growing up, and now demands regular, personalized gifts? Then: I had an affair with my pastor, and just met the daughter I g...Show More

Dear Prudence: The “Missing the Point” Edition

38:24 | Nov 22nd, 2016

If you see dirty pictures on someone else’s phone, that’s your problem. And a reminder: Dear Prudence is not a tax attorney, and neither is her guest, Toast co-founder Nicole Cliffe. Your questions today revolve around missing the mark. I’m always th...Show More

Dear Prudence: The "Either/Or" Edition

42:37 | Nov 15th, 2016

A note on the election and the limits of civility. Then, religion, inheritance, sibling rivalry: Prudie and guest Noah Kulwin discuss binaries. If you’re not close with your nephew, should you give him your old car instead of gifting it to your godda...Show More

Dear Prudence: The "How Long?" Edition

44:03 | Nov 8th, 2016

Queer women, Carly Rae Jepsen, and what’s up with people confessing crimes on Facebook? Prudence and guests Jaya Saxena and Matt Lubchansky take on your problems of timing, including: do you have to let your fiancé’s ill mother live with you indefini...Show More

Dear Prudence: The “Whaaaattt?!?” Edition

42:30 | Nov 1st, 2016

A listener offers her guide to figuring out if the white guy she’s dating has an Asian fetish. Then, Prudence and writer Brook Shelley get to your letters. First up, a mixed-race letter writer is dismayed to wake up to chain of racist texts — sent by...Show More

Dear Prudence: The "Good Intentions" Edition

32:24 | Oct 25th, 2016

Nancy Ortberg, AKA Mallory’s mom, joins us for questions today. How do you to talk to a stepdad who tries to boost your confidence by making borderline-creepy remarks about your appearance? What do you say to stop your parents from complaining to you...Show More

Dear Prudence: The "Devil's Advocate" Edition, Part 2

35:28 | Oct 18th, 2016

Carvell and Mallory jump right back in. A letter-writer complains that her brother is a “man whore” — but first, we need to talk about who’s throwing glass at your family events. Then, should I tell my fiancé that I’m pretty sure I once slept with hi...Show More

Dear Prudence: The "Devil's Advocate" Edition, Part 1

38:18 | Oct 11th, 2016

Just say no to the “Don’t Tread On Me” snake. Mallory and returning listener favorite Carvell Wallace tackle and disagree over thorny questions like: should you intervene when your sister invites your mom to her wedding — but not your stepdad? When y...Show More

Dear Prudence: The "Boundaries" Edition

41:44 | Oct 4th, 2016

This week, your questions discussed in the cozy setting of Prudie’s literal bedroom. That might sound overly-intimate, but it’s not as intimate as going to a sweat lodge with your coworkers! Our guest is writer Lauren O’Neal, and together she and Pru...Show More

Dear Prudence: The "Creative Solutions" Edition

36:29 | Sep 27th, 2016

Ann M. Martin and the gay Baby-Sitters Club, plus some unsolicited advice to a letter-writer who’d like to ruin his sons’ lives from beyond the grave and can’t find a lawyer to help him do it. SkyMall nostalgia. Then, Prudence and guest Rebeca Sanche...Show More

Dear Prudence: The "Talk About It Now" Edition

43:59 | Sep 20th, 2016

The great lie that is, “they don’t really mean it.” Mallory and her sister, writer Laura Turner, bring some family wisdom to this week’s show. First: is it alright to ask your family to stop texting you the news of relatives’ deaths? What about when ...Show More

Dear Prudence: The "Petty Revenge" Edition

35:05 | Sep 13th, 2016

End the tyranny of the snooze button. Prudie and writer Mikki Kendall answer your questions, and let’s just get one thing out of the way right now: don’t try to attempted-murder Mikki by turning on an electric fence while she’s touching it; that won’...Show More

Dear Prudence: The "Do it In Song" Edition

34:34 | Sep 6th, 2016

Comedians W. Kamau Bell and Hari Kondabolu of the podcast Politically Re-Active join Prudie to dispense advice — sometimes in song! — about how to get a needy ex out of your house, how best to deal with a deadbeat husband, and how to figure out if yo...Show More

Dear Prudence: The "Time is Not an Apology" Edition

35:16 | Aug 30th, 2016

Prudence and guest Lisa McIntire on when you should rock the boat, why people feel entitled to be rude to their friends, and how time passing does not equal an apology. First though, you should go see Bad Moms… the audience, that is. More thoughts on...Show More

Dear Prudence: The "Little Red Hen" Edition

33:28 | Aug 23rd, 2016

A woman dropped family, friends, and job to move across the country for a relationship that didn’t work out — and things got worse from there. Is she doomed to make poor decisions for the rest of her life? A man dies, and his obituary lists a woman w...Show More

Dear Prudence: The "Read the Room" Edition

28:35 | Aug 16th, 2016

Prudence flies solo and argues with — or against — her better angels. She anoints the Worst Commercial of the Year and advises a woman wondering if she has to let a family member with money trouble live in her empty investment apartment. But Prudie l...Show More

Dear Prudence: The “Self Indulgence vs. Self-Care” Edition

33:14 | Aug 9th, 2016

Does HR really work for employees — or is it just there for the company? Prudence shares a listener perspective. Then, Prudie and friend of the show Jos Lavery counsel a woman who’s essentially written in just to say how great her life is. A listener...Show More

Dear Prudence: The "You Can’t Treat People That Way" Edition

30:29 | Aug 2nd, 2016

Jasmine Guillory is back in the studio with Prudie to talk about how to handle a partner who doesn’t believe in antidepressants, counsel a woman in an emotionally abusive relationship with a physically disabled man, and, for a bit of relief, adjudica...Show More

Dear Prudence: The Unconditional Love Edition

38:54 | Jul 26th, 2016

Today’s questions are about life’s unfairness and the meaning of unconditional love; Dear Prudence and writer Carvell Wallace roll up their sleeves and get tough. A woman writes with a question about what she owes her troubled, and now-adult, adopted...Show More

Dear Prudence: The "Butt Out" Edition

24:47 | Jul 19th, 2016

Mallory and Slate’s Aisha Harris talk about butting in where you don’t belong. Should you call Child Protective Services because you think someone’s kids aren’t learning enough algebra? How do you deal with a colleague making inappropriate remarks ab...Show More

Dear Prudence: The "Regret Baby" Edition

32:14 | Jul 12th, 2016

Dear Prudence and Slate’s Christina Cauterucci take on behavior that goes from bad to worse: a “toxic friend” who uses her mental health issues to get away with abusing her friends; a man trying to shame his wife into having a “regret baby” seven yea...Show More

The "Transactional Relationships" Edition

21:30 | Jul 5th, 2016

Mallory Ortberg and guest Jos Lavery discuss why we feel so compelled to discuss human relationships as transactions, and discuss how to handle family members who might be committing insurance fraud.

The "Sisters!" Edition

21:35 | Jun 28th, 2016

How do you tactfully let your sister know it’s time for deodorant? Or that you hate her dog? And how do you protect your sister from your overbearing parents? This week, Mallory Ortberg and guest Jasmine Guillory bring their advisory, legal, and chil...Show More

The "Is This a Real Question?" Edition

28:57 | Jun 21st, 2016

Mallory assesses the emotional fitness of people who spill drinks on themselves and tackles your questions with Alison Green of Ask a Manager. Is the letter about "a series of Spider-Man piss revelations" real or fake? How do you manage a recently du...Show More

Coming Soon: Dear Prudence

01:55 | Jun 13th, 2016

Every week, Mallory Ortberg (aka Dear Prudence) tackles problems about love, life, and everything in between.