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



Wednesday Jan 17, 2024
101 | Gobsmackedly
Wednesday Jan 17, 2024
Wednesday Jan 17, 2024
This week, the Biffs catch up with Carolyn Hax’s column on the Washington Post. A friendship that should stand the test of time doesn’t when one’s expectations go unmet. Weed - it’s what’s for dinner - and this dinner guest can’t keep their balance long enough to communicate their frustration over crossed boundaries. Dad’s playing sugar daddy while mom’s working extra hard to keep up with the bills on the heels of retirement. [Babich Sauvignon Blanc, 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 Jan 10, 2024
100 | Is She Manspreading?
Wednesday Jan 10, 2024
Wednesday Jan 10, 2024
In their one-hundredth episode, honorary Biffs (the West Coast Biffs) Rachel Sievers and Ellie-the-Editor of the Answer to Everything Podcast, join Stefani and Ray to celebrate with a bottle of champagne. Ben is surprised and intrigued by his alter-ego Britney. Competitive tooth-brushing masks a fictional couple’s real issues. Cyber-ghosts haunt an imaginative and creative internet surfer. Join this foursome as they take on the internet with some “unrealistic, psychologically unsound scenarios” and responses generated by ChatGPT. Hate it. Love it. [Maybe] learn something? [Veuve Clicquot]
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 Jan 03, 2024
99 | Best of the Biffs (Part III)
Wednesday Jan 03, 2024
Wednesday Jan 03, 2024
Happy New Year. This week's episode reflects on some of the best of 2023, as we work up to our centennial episode. Listen on and revisit more of their favorite columns, with questions from Ask Logan, Ask Daddy, and the Ethicist. A husband hides his wife's only form of sexual pleasure. A writer's partner wants to be his boyfriend when out and about, but prefers the pronoun "she" in private. An author questions her own ethics as she debates whether the murder she was a witness to is fair-game in her profession.
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 Dec 27, 2023
98 | On a Scale from One-to-Bang
Wednesday Dec 27, 2023
Wednesday Dec 27, 2023
It's back to the Slate's "Dear Prudence" column for Stefani & Ray this week. A whole family dynamic shifts when a man decides against donating another sample of his own sperm to his sister and her wife. When another man's brother and best-man's tendency to hire escorts for dinner is exposed, his fiancee's reaction threatens to end their engagement. Lastly, a writer is angered and perplexed with their partner's self-diagnosed autism. Listen to the Biffs weigh-in on these complex issues. [1000 Stories Bourbon Barrel Aged Red, 2018]
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 Dec 20, 2023
97 | 33% Effective at Raising Children
Wednesday Dec 20, 2023
Wednesday Dec 20, 2023
In this week's episode, the Biffs read from Annie Lane's Dear Annie Column. A wife's secret sexual past leaves her husband of fifty years searching for the deep intimacy that once connected them. An adult couple is forced to exist behind closed doors when a man's family refuses to accept his girlfriend, for reasons unknown. A man struggles to find refuge in his girlfriend when she weaponizes his emotions for his dead wife for leverage in the relationship. [Ghost Pines Cabernet Sauvignon, 2020]
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 Dec 13, 2023
96 | Didn’t Mean to ’Jennifer-Coolidge’ You
Wednesday Dec 13, 2023
Wednesday Dec 13, 2023
The Biffs test their skills against advice from Coleen Nolan of the Mirror UK. A mother with knowledge of her daughter’s beau’s past questions whether to tell her or not. A man places a camera in the shower in hopes of spying on his wife and ending his 15-year-dry-spell. Finally, a woman meets a man at a wedding and suddenly she wants more than what her husband can offer. [Gualdo del Re Sangiovese, 2012]
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 Dec 06, 2023
95 | I’m a Ventriloquist?
Wednesday Dec 06, 2023
Wednesday Dec 06, 2023
This week, the Biffs read from Reddit’s Am I The Asshole. A parent’s personal choice results in their child’s bullying and his shifting the burden to another family member. At a college party, a personal question about his penis prompts a writer to respond with a similar personal question about a co-ed’s level of baldness down-south. Navigate these interesting social situations with Stefani and Ray as they judge if these Redditors are assholes. [Novinophobia Chardonnay, 2018]
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 Nov 29, 2023
94 | Took My Pants Off to Cry
Wednesday Nov 29, 2023
Wednesday Nov 29, 2023
This Biffs regrettably follow-through with last week’s promise to revisit Cary Tennis’s advice column from Salon.com. Stefani and Ray differ in opinion on how to handle a situation when a baby sister is discovered to have a criminal record. A man transfers some of his angst and grief onto his partner following the passing of his ‘monster’ of a mother, and he doesn’t even see it. [The Pale Rosé, 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