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 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 2021 Chenin Blanc]

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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 2022 Rose]

 

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June 27, 2024 55 mins

In this week’s episode of Ill Advised, Stefani and Ray read from Miss Manners column from UExpress. One writer asks for help in determining when to relate and when to express empathy when someone close is sharing a personal problem. Another writer takes a tumble and becomes the joke of the friend group. Finally, a change in a cancer survivors appearance has them wondering how to redirect compliments. [Chateau Laborde ...

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June 20, 2024 47 mins

It's another trip down memory lane as we relive some our favorite advice columns from our early days. From episode 13 - Swipe if You Want the Pipe, the Biffs address a writer's plan to get down and dirty with an internet beau. A man's uncut member becomes a Jewish mother's biggest worry, in episode 32 - Was Jesus Circumcised. And from Episode 72 - In the Privacy of Your Public, should Mom have knocked when the son uncharacteristica...

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June 13, 2024 51 mins

Coleen Nolan, the Mirror.co.uk's agony aunt's column, is the topic of this week’s conversation between the Biffs. A woman’s insecurities over the life her daughter lives prompts her question to Coleen. Another woman’s husband doesn’t like it when she’s barefoot on vacation, when she just wants to air out the puppies. Finally, when your Biff doesn’t like your significant other, which side of the fence do you play on? [...

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June 6, 2024 60 mins

The Biff’s read through advice from Jenee Desmond-Harris of the Slate’s Dear Prudence, this week. A woman finds her husband’s notes to himself on the best way to handle her in several scenarios. A husband cheats on his wife with the person she has a restraining order on, and now she’s ready to give notice at their co-owned business. Lastly, when the rat-tail when out of style, this writer thinks their baby book should...

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In this week’s episode, Stefani and Ray read from “Dear Abby.” A woman struggles to support her daughter through divorce when she learns about their open marriage. An ornate cut glass cake stand is the final straw after a writer feels snubbed by their family friend. Finally, a young woman is torn about her parent’s divorce after her father lays blame directly on her. [Rapaura Springs 2022 Sauvignon Blanc]

 

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May 15, 2024 42 mins

Out of the Vault: This week, the Biffs bring you an episode with unaired segments from previous recordings. From Boston Globe's Love Letters, Stefani and Ray discuss a twenty-four years old's serial monogamy and her plea to ditch the habit. From The Slate's How To Do It, the Biffs learn about garden party- and kitchen table-polyamory when a writer's efforts at having all of their partners at their birthday party are stalled due to ...

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May 8, 2024 53 mins

The Biffs take on Reddit’s Am I The Assh*le again this week. A man’s culinary skills are challenged when his sister’s boyfriend marches out in a huff in search of his own hot sauce. When a man is sniffed by a dog at a pet-friendly eatery, he barks at it’s owners. Self-sufficiency is a lesson best learned at self-check out. Finally, a grown man is butt-hurt and lashes out against his girlfriend’s daughter for referring...

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May 1, 2024 62 mins

In this week's episode, the Biffs, Stefani and Ray, read from the Reddit Am I The Asshole (AITA) thread. A man begs for judgement after serving his stay-at-home-mom wife with a performance evaluation based on the way she parents their children. Another Redditor brings her case before the internet after her roommate snitches on her to the landlord for refusing to move her sofa. [Miguel Vinho Verde]

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April 24, 2024 68 mins

Sally Land's Dear Deidre of the Sun.co.uk takes the stage this week, with some controversial advice topics. What do you do when the man of your dreams turns out to be your long lost half-brother - and you want to keep sleeping with him? A man is pocket dialed by his wife and listens in to her moans and groans before busting her at home. A love child threatens a family's livelihood. [Bonterra 2021 Zinfindel]

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April 17, 2024 73 mins

Natalie Bencivenga’s "Ask Natalie" is the center of the Biffs' conversations this week. It’s one thing to sleep with your best friend’s boyfriend, but it’s another thing entirely to keep it from her. A man questions his fidelity after hiding a sex toy purchase from his ailing wife. Finally, a cheating husband wants to have a sleepover with his mistress where he and his wife still live and share a home. It’s an episode...

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April 10, 2024 51 mins

In this week’s episode, Stefani and Ray read from Boston.com’s Love Letters, by Meredith Goldstein. A retreat from the familiar and the mundane inspires a left-field marriage proposal that the first writer only sees as a bandage to their problems. In the second letter, a woman introduces her boyfriend to her mother only to find out about their past sexual relations. Listen on to see what the Biffs have to say [Oyster Bay 2022 Pinot...

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