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 Mar 20, 2024
110 | Do You Take Dick King?
Wednesday Mar 20, 2024
Wednesday Mar 20, 2024
In this week’s episode, your Biffs talk advice from How to Do It’s (Slate.com) Rich Juzwiak. In the first question, the Biffs discuss a scenario where ex-lovers, apart for thirteen years, come back together only for one of the men to be completely put off by his roommate's comfortable appearance. Lastly, a woman is having a hard time trusting her husband when she uncovers his lies and his hidden panty and anal sex toy fetish. Stefani and Ray also talk red flags: Who’s are they? [The Dreaming Tree Pinot Noir, 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 Mar 13, 2024
109 | Intersmooshes
Wednesday Mar 13, 2024
Wednesday Mar 13, 2024
Stefani and Ray read from the Ask Amy advice column. A writer questions her dying father-in-law’s legacy, when his reputation as a cop is tainted. Another asks about her friend’s penchant for venting on social media and whether she should approach her about it. Finally, a woman finds a secret life on her boyfriend’s cell phone, post-mortem, and can’t bring herself to mourn his passing. [Chateau Blaignan Red Blend, 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 Mar 06, 2024
108 | Under the Red Rock
Wednesday Mar 06, 2024
Wednesday Mar 06, 2024
The Biffs read from the classic Dear Abby column this week. A woman weighs the fairness of her husband’s ultimatum to choose between him or their son and his family. Another contemplates contacting her sweetheart’s other girlfriend just so that she knows she exists. A woman in a long-term relationship questions everything when her daughter and her partner’s son fall in love. The last writer wonders what to do about her sister’s knack for telling outrageous stories. [Harken Chardonnay, 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 Feb 28, 2024
107 | "Red-Wings" or Plummet
Wednesday Feb 28, 2024
Wednesday Feb 28, 2024
In this week’s episode, the Biffs read from Zachary Zane’s Explain It Column from MensHealth.com. One man finds it hard to submit to his sexual desires when his not-sex-positive Mom who is all up in his business, is tracking his location. An older woman orders out frequently in hopes that she’ll one day get the nerve to seduce her delivery boy. Finally, a man ask’s for guidance in a situation where his girlfriend limit’s sex to two weeks per month, when he’s perfectly comfortable with sex during her cycle. [Amigo Perro Cabernet Sauvignon, 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 Feb 21, 2024
106 | Are You as Good as Your Papi?
Wednesday Feb 21, 2024
Wednesday Feb 21, 2024
Stefani and Ray visit Natalie Bencivenga's, Ask Natalie column, in this week's episode. An engaged woman, three years into her relationship, questions her fiancé’s position against meeting her future in-laws. A woman is shamed by her friends when she wants to ghost on the man she’s been dating, after their first time in bed together. A sister’s drunken attempt at her brother-in-law, causes another writer to question helping her live-in, struggling sibling at all. [Château LaBorde 2Bordeaux Sauvignon, 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 Feb 14, 2024
105 | He. Him. Wrong.
Wednesday Feb 14, 2024
Wednesday Feb 14, 2024
Stefani and Ray take questions from the Facebook group, "High Value Feminine Women," in this week's episode. One woman reaches out to ask for advice in her relationship and winds up talking herself out of it mid-post. Another finds pictures of her man with his ex-wife, with whom he has a child, and questions the validity of the feelings she’s experiencing. Finally, the Biffs discuss another writer's question about standards and expectations in relationships, and how to tell the difference between the two. [Whispering Angel Rosé, 2019]
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 Feb 07, 2024
104 | Full Butth*le Present
Wednesday Feb 07, 2024
Wednesday Feb 07, 2024
This week's episode is mini, but fun. The Biffs revisit Reddit's Am I the Asshole Thread. A man asks if he's a jerk for telling his aunt that her man's given up on her when she asks for advice. Another is put off by a yogi's theatrics in the sauna, as he downward-dogs and spreads without so much as a loincloth. Make sure to join us next week as we continue our dive into this thread. [Josh Prosecco Rosé]
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 31, 2024
103 | If Water Had a Taint
Wednesday Jan 31, 2024
Wednesday Jan 31, 2024
Stefani and Ray visit the Metro.co.uk’s Agony Aunt, Em Clarkson, in this week’s episode. A writer worries about their best friend’s borderline obsession with her beau. One half a relationship has absolutely had it, but doesn’t know how to tell her husband that it’s over. OnlyFans becomes a topic for debate among the Biffs when a woman feels betrayed by her boyfriend after discovering his subscription. [Bota Box Sauvignon Blanc]
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