Ill Advised with Stefani & Ray

Ill Advised with Stefani & Ray

Ill Advised with Stefani and Ray is a comedy-advice podcast where friendship meets life’s messiest situations. Each week, the BiFFs dive into classic and modern advice columns — from the sincere & genuine to the unhinged & absurd — and serve up their own brand of thoughtful, unfiltered advice, the way only a best friend could. If you like living through someone else’s drama, emotional deep-dives, and laughing through life’s inconveniences, this one’s for you. Join the BiFFs — Stefani & Ray — as they dig into advice columns and dish out their own insights with humor, heart, and a whole lot of therapy under their belts. Come for the laugh. Stay for the advice. Therapy-adjacent, wine-fueled, and probably ill advised.

Episodes

August 20, 2025 63 mins

Out of the Vault: A wife’s uncomfortably close bond with her stepdad has her husband spiraling; a boyfriend thinks a lie detector is the secret to lasting love (and they say romance is dead); and a sister is ready to go to war with her late brother’s abusive widow. Stefani and Ray dive headfirst into the drama of Dear Abby, serving up side-eye, sharp takes, and just enough empathy to make it sting. Expect boundary violations, a lit...

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Out of the Vault: The summer vacation continues with another unreleased recording. A hidden video. A bizarre bedroom ultimatum. And the Sunshine State taking its “Florida Man” energy straight to the law books. This week, the Biffs wade into three deeply unsexy messes from Slate’s How to Do It column: the girlfriend who found exactly what her boyfriend didn’t want her to see, the woman stuck with a partner whose idea of foreplay com...

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August 6, 2025 57 mins

Out of the Vault: Previously recorded and unaired, this week the Biffs read from Ask Natalie. He’s married. You’re pregnant. And he thinks the solution is as easy as hitting delete. Then, your bestie’s open marriage suddenly includes your husband—and no one asked your opinion. This week, Stefani and Ray dive headfirst into the kind of chaos that makes you want to throw your phone in the ocean. Expect enough boundary violations to w...

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July 30, 2025 57 mins

A mistress meet-cute at the nail salon. A stolen baby name (the audacity!). And a Golden Corral showdown that wasn’t even their first. This week, the Biffs tackle three delightfully deranged dilemmas from Slate’s Dear Prudence column, including: what to do when you and your boyfriend’s side piece go full spy-movie, whether baby names are fair game (spoiler: not if you’re a traitor), and how to cope when your in-laws t...

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A disappearing best friend who still lurks in case she needs something. A guy who shoots his shot via BCC. And a man losing sleep because his girlfriend’s on OnlyFans. This week, the Biffs dig into three very relatable modern-day dilemmas pulled from Love Letters: the blurred line between ghosting and passive-aggressive friendship, the wild west of digital dating etiquette, and the fragile male ego in the face of empowered women. A...

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July 9, 2025 59 mins

This week’s mess includes backne, breakups, and body lotion masquerading as soap. Stefani and Ray dive into four gloriously messy AITA questions: the guy who asked his sister-in-law to sunscreen his bacne, the girlfriend who gave her boyfriend the crop treatment (literally), the almost-stalker who let a stranger cry it out, and the man who’s been washing his hands with body lotion for three weeks straight.

After listening to these ...

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July 2, 2025 67 mins

Love is hard. Boundaries are harder. And your boyfriend’s about to cry again. This week, the Biffs dive into three emotionally chaotic conundrums: what to do when the dating drought has you questioning if marriage is even in the cards, how to end things with your boyfriend without emotionally wrecking him, and how to draw the line with your dad’s new wife without blowing up the family group chat. Stefani and Ray bring...

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June 25, 2025 64 mins

A psychic says dump him—so should she? This week, the Biffs dive into three very modern meltdowns, from The Independent's Dear Vix Column. trusting tarot over your own intuition, obsessing over your boyfriend’s ex (oops), and losing a friend to her walking red flag of a man. Stefani and Ray bring their signature best-friend banter and wine-fueled wisdom to the mess, offering emotionally honest (and very unlicensed) advice to the ro...

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June 18, 2025 59 mins

This Biffs read from R. Eric Thomas’s advice column this week. A writer’s distrust in their second husband has them questioning if they should contact the first wife to get their real story. Another writer's sister-in-law loads up her car with her own thoughts of her inheritance following their parent’s death. Finally, tensions run high when a man’s one night stand resurfaces after forty-three years, shacking up with ...

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June 11, 2025 64 mins

This week, the Biffs read from Natalie Bencivenga’s Ask Natalie. What’s the correct course of action when your husband’s empowered to be more controlling as a result of the presidential election? Oldest friend may not mean best friend, but should you still help plan their birthday? Pregnant, and now your abusive boyfriend wants to get married?  [Natale Verga Gavi, 2023]

Send us your questions, feedback, ...

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June 4, 2025 60 mins

After a ten-month hiatus, your Biffs are back! Stefani and Ray hit the waves refreshed with new questions and the same banter. This week, the Biffs take on the Slate’s “How To Do It.” A girl know’s too much about a new girlfriend’s boyfriend’s past, and is chomping at the bit to tell her. A man is turned on when he finds out his boyfriend is married, and wants to look the other way. A man’s fetish for golden showers is anything but...

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August 28, 2024 57 mins

Stefani and Ray visit Susan Writer's column, Ask Someone Else's Mom, this week. The Biffs read about potentially rigged, by-chance encounters with former flames; an inter-familial rivalry that has two uteruses vying for first; and a long-distance open relationship without rules on track for marriage. [Patrice Grasset Vin de France Chenin Blanc, 2021]

Send us your questions, feedback, &/or wine recommendations to i...

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August 21, 2024 70 mins

In this week's episode, relive some of the Biffs' favorite moments of Ill Advised. From episode 78 - How to Kidnap Us, a man's self-proclaimed stupid face is putting his wife off to sex with him. In episode 11 - God Damn It, Kourtney, her partner's weight gain has a woman questioning the future of her relationship. And from Episode 22 - Dick, Thom, & Beelzebub, a woman's lackluster sex life leaves her wondering if she can have ...

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August 14, 2024 40 mins

Out of the Vault: This week, the Biffs bring you an episode with unaired segments from previous recordings. From Reddit’s AITA, a father wonders if laughing at his son’s self-sabotage makes him an asshole. From Metro.co.uk, a man promises to suppress his homoseuality in exchange for shelter with his wife and their children. And from Ask Amy, a woman starts a Facebook dating profile after her husband does, but is asked...

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August 7, 2024 78 mins

In this week’s episode, the Biffs read from one of their favorite columns -  Natalie Bencivenga’s, Ask Natalie. A series of unfortunate events in a contentious relationship leaves a grieving widow wanting to sever ties with her late husband’s son. A writer’s roommate-turned-close-friend crosses an unspoken boundary and violates her privacy when she borrow’s her sex toy. Another writer’s emotional capacity to handle he...

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July 31, 2024 62 mins

Stefani and Ray attempt to weigh in on questions sent to the Slate.com’s How To Do It Column, by Rich Juzwiak and Jessica Stoya. A coupled individual’s want to connect intimately with girlfriends is interrupted by booty calls and one-nighters. Another writer’s realization that they’re non-binary, along with their penchant for masochism, leaves them wondering if their husband is the one for them. Finally, a woman’s att...

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This week, the Biffs revisit Reddit’s Am I the Assh*le (AITA) thread. A man’s disagreement with his wife’s unusual punishment of their underaged drunk son stalls communications at home. Another father questions whether he’s asshole for kicking his son out, when it’s revealed that he’s been staying with them because he cheated on his pregnant, bed-ridden wife. And a man’s dash cam footage reveals what he really did to ...

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The Biffs, Stefani and Ray, put new columnist, R. Eric Thomas of Asking Eric (Washington Post), to the test. He’s got big shoes to fill as he steps in following Amy’s (Ask Amy) departure. An anti-gay rights in-law puts together a family tree and leaves the writer’s husband of ten years out, because of her stance on same-sex marriage. A man who enjoys just about everything in his marriage can’t stomach another one of h...

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July 10, 2024 55 mins

The Biffs celebrate twenty-one years of Ask Amy with a send-off/tribute, including some of her best advice to date. Amy gets pranked in our first question, when a writer's scenario is the movie plot of the 2003 cult-classic, The Room. The second writer is a woman whose unchecked privilege, along with that of her family/friend group, gets in the way of her being a good sister. Finally, a dinner guest is upset following a party where...

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July 3, 2024 53 mins

This Biffs read through Laura Collins's column in the Metro.co.uk this week. One writer asks for guidance on coming out to her mother about sleeping with her uncle. Another questions that status of his marriage when his postpartum wife cheats on him, following his unplanned vacation with his friends. And finally, a young man, sexually harassed by his dad's young girlfriend, doesn't know how to tell him. [Prophesy Rosé, 2022]

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