Ill Advised with Stefani & Ray

A fiancé in love with his AI “girlfriend.” A food influencer who turns a first date into content. A boyfriend who live-streams arguments for likes. This week, the Biffs dig into three Ask Natalie letters that prove dating has gone full Black Mirror. Between the clout-chasing, the codependency, and the collective loss of shame, Stefani and Ray ask the real question: is there any love left that doesn’t need an audience? [Gran Passione Pinot Grigio, 2023]

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Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

This week, Stefani and Ray put the advice column down and turn the spotlight on themselves—answering the kind of unhinged, cockamamie questions only ChatGPT could dream up. From ghosting for the pettiest reasons to drag-naming their unresolved trauma, the Biffs get brutally honest and painfully funny about their own mess. Turns out, nothing makes you face yourself quite like bad hypotheticals and mediocre wine. Get prepped for maniacal self-reflection, but don't judge them. Ray doesn't have time for this and Stefani forgot to shave. [Louis Jadot Beaujolais-Villages, 2023]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

Lies, loathing, and a whole lot of family baggage—it’s a triple feature in this week’s episode when the Biffs read from the Independent's Dear Vix column. First, a compulsive storyteller whose “white lies” have evolved into full-blown epic sagas. Next, a mom who swears she’d take a bullet for her daughter… but would rather not take her to brunch. And to round it out, someone finally blurts the unspeakable: they just don’t like their parents (yes, even after the holidays).

Stefani and Ray roll up their sleeves and dive headfirst into the dysfunction, serving up therapy-adjacent hot takes like “maybe stop lying so much,” “boundaries are cheaper than bullets,” and “you don’t have to like family just because DNA says so.” It’s messy, it’s brutally honest, and it’s exactly the kind of chaos that makes you feel a little better about your own group chat. [Four Vines Old Vine Zinfandel, 2021]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

A nosy neighbor, a leaked sex tape, and a family secret one spit tube away from detonating—welcome back to Prudie’s wild ride [Dear Prudence, Slate.com. This week, the Biffs tackle three disasters in the making: a kid who takes revenge on a cop-calling neighbor, a risqué video that lands in the wrong inbox, and DNA test results that could unravel a whole family. Stefani and Ray weigh in with their usual mix of chaos and clarity, doling out advice so unlicensed it should probably come with a warning label. Tune in and let us ruin your problems before you ruin them yourself. [Louis Jadot Beaujolais-Villages, 2023]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

This week, Colleen Nolan’s (Mirror.co.uk) inbox is a circus and we’ve got front-row seats. A man secretly pays off his wife’s ex-husband like it’s hush money for his own conscience. A woman brags about cheating on her husband with a coworker and somehow thinks “no guilt” is a personality trait. And another poor soul can’t stop dreaming about a high school crush while insisting she’s totally happy in her marriage. [Martin Codax Albarino, 2024]

Consider it your weekly reminder that love lives are messier than a group chat after bottomless brunch—and Stefani and Ray aren’t here to clean it up, just to make sure you don’t look away.

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

Out of the Vault: One bride’s recycling her heartbreak couture, another diner’s beefing with the blue-plate special crowd, and someone’s about to ghost a group chat with more drama than a telenovela. This week, the Biffs weigh in on three Am I the Asshole (Reddit) posts that range from petty to petty iconic: should you wear the dress even if it was meant for your ex, clap back at elderly buffet bullies, or leave a group chat that just won’t die? Stefani and Ray bring eyebrow-raises, unlicensed logic, and just enough judgment to keep you from pressing send. [Franck Massard Mas Sardana Brut Nature Cava]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

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 little family chaos, and at least one (or three) piece of advice Abby definitely wouldn’t co-sign. [Samuel Robert Pinot Noir Rosé Vineyard Reserve, 2023]

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 comes with fine print, and the Floridian whose favorite solo pastime is now on the state’s naughty list. You’d think Stefani and Ray were Attorneys at Flaw at Policy, Privacy & Pleasure—but with more judgment, less restraint, and better wine.[Château La Freynelle Bordeaux Blanc, 2023]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

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 warrant a cease-and-desist. [Juggernaut Sauvignon Blanc, 2023]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

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 treat buffet night like WrestleMania. This one’s got all the essentials: espionage, betrayal, and buffet brawls. But don’t worry—Stefani and Ray came armed with side-eyes, hot takes, and at least one grudge. [Famille Bougrier Sauvignon Blanc Val de Loire, 2024]

Send us your questions, feedback, &/or wine recommendations to [email protected].

Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com