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
Episodes



Thursday May 30, 2024
119 | Ketamine. Okay, We'll Start Here.
Thursday May 30, 2024
Thursday May 30, 2024
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 Sauvignon Blanc, 2022]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday May 15, 2024
118 | You're a Glory Hole
Wednesday May 15, 2024
Wednesday May 15, 2024
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 group dynamics.
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday May 08, 2024
117 | Runneth-Up, B*tch
Wednesday May 08, 2024
Wednesday May 08, 2024
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 to him as creepy during school drop-off. [Casillero del Diablo Sauvignon Blanc, 2022]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday May 01, 2024
116 | Unauthorized Stripper Pole
Wednesday May 01, 2024
Wednesday May 01, 2024
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]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday Apr 24, 2024
115 | Forgive Me, Father
Wednesday Apr 24, 2024
Wednesday Apr 24, 2024
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 Zinfindel, 2021]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday Apr 17, 2024
114 | Not a Sex Doll Movie
Wednesday Apr 17, 2024
Wednesday Apr 17, 2024
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 of anecdotes and witty banter between Stefani and Ray. [Skouras Moscofilero, 2021]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday Apr 10, 2024
113 | The Whole Wrinkled Penny
Wednesday Apr 10, 2024
Wednesday Apr 10, 2024
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 Pinot Gris, 2022]
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com



Wednesday Apr 03, 2024
112 | Best of the Biffs (Part V)
Wednesday Apr 03, 2024
Wednesday Apr 03, 2024
In Best of the Biffs (Part V), listen to some of Stefani and Ray’s favorite questions from episodes 82 - Lemme Project These Hands, 79 - Polly Want a Condom, and 73 - Mt Me Beautiful. A man’s mismatched sex drive has him asking Natalie Bencivenga if opening his marriage is a good idea. ChatGPT gives the Biffs a wild scenario of a parrot blabbing about their owner all over the neighborhood. Eleanor Gordon-Smith publishes a response to a woman who’s witnessing the return of the mistress that ruined her marriage.
Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com.
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com