Ill Advised with Stefani & Ray

This week, the Biffs serve up a best-of compilation of some of our most unhinged, emotionally loaded, and “oh wow we really said that” advice moments. From Ask Natalie dilemmas about a partner sliding into control after Trump’s re-election and finding out your best friend knew about your husband’s affair, to one Slate How To Do It scenario that fully redefined the phrase “family issues.” Stefani and Ray revisit the mess with fresh eyes, sharper boundaries, and the same wine soaked wisdom you’ve come to expect. Consider this your reminder that the advice was wild, the takes still hold up, and yes, some red flags really are timeless. 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.

Is he private… or are you a secret? This week, the Biffs crack open Ask Natalie and dive into three modern relationship nightmares: a boyfriend who won’t acknowledge your existence, Venmo emoji payments to a suspicious “gym friend,” and a best friend who hates you like it’s her full-time job. Stefani and Ray unpack the power plays, the plausible deniability, and the quiet moments where your nervous system is already screaming the truth. [Doña Paula 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.

This week, the Biffs dive into Coleen Nolan’s Mirror column and immediately ask: should we be allowed to know this much about strangers? We’ve got forbidden fantasies about a fiancé’s sister (ma’am??), a working parent doing pre-shift cocaine while the kids remain blissfully unaware, and a grief dilemma where “respecting wishes” collides with “I still need closure.” It’s horny, dark, sad, and somehow funny — and Stefani and Ray do what they do best: spiral, empathize, roast (gently), and offer extremely unlicensed advice along the way. [Lagaria Pinot Grigio, 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.

This week, the Biffs drop into Reddit’s Am I the Asshole?, where feelings are inconvenient and accountability is theoretical. A man asks his wife to stop crying in a Home Depot like it’s a customer service issue, another apologizes to his mom for his wife to keep Family Day “smooth,” and a friendship detonates when a dog eats someone else’s meds and a $1,500 vet bill shows up demanding answers. Stefani and Ray tear into public tears, peacekeeping that looks a lot like betrayal, and the eternal question of modern adulthood: when everything goes sideways, who’s actually responsible? Come for the chaos. Stay for the verdicts. [Juggernaut Russian River Pinot Noir, 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.

This week, the Biffs crack open The Washington Post’s Carolyn Hax column and immediately regret having functional nervous systems. We tackle a family who keeps serving seafood despite a life-threatening allergy (because vibes > survival, apparently), a woman wondering if it’s fine to marry a man she’s not excited about as long as he’d make a solid dad, and a soon-to-be father who went bungee jumping and was shocked to discover his very pregnant wife was not amused. Stefani and Ray bring their usual best-friend banter, emotional honesty, and low tolerance for nonsense as they talk boundaries, risk, resentment, and why “it seemed like a good idea at the time” is not a personality trait. [Colossal Reserva Red, 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.

This week, the Biffs dive into Lizzy Acker’s Why Tho? column, where the drama is feral, the boundaries are theoretical, and everyone’s courage seems to come from a mysterious off-brand energy drink. We’re talking: a wife who unilaterally opens her marriage and detonates an entire friend group, a boyfriend who wants to “gently” tell his girlfriend her facial hair is ruining his life (spoiler: there is no gentle version), and a 20-year friendship that ends with a breakup email so cold it should come with frostbite warnings. Stefani and Ray unpack the chaos with their trademark banter, hot takes, and unsolicited-but-deeply-felt advice for the romantically bewildered. [Squealing Pig Sauvignon Blanc, 2023]

This week, the Biffs tackle Thanksgiving chaos courtesy of Dear Prudence and Dear Abby: one man is appalled his wife wants to help the less fortunate on a holiday (unthinkable), and one older sister is being roped into cooking the entire feast for a sibling who’s “hosting” in name only. Stefani and Ray bring peak sarcasm and zero patience for seasonal nonsense. Expect righteous indignation, a touch of holiday guilt-tripping, and the annual reminder that family gatherings are just team-building exercises with higher stakes. [Côté Mas Orange, 2024] 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.

This week, the Biffs dive into Slate’s How To Do It, where the sex is messy, the signals are mixed, and every letter reads like it was written mid–panic spiral. We tackle: a husband rattled by a “joke” from his wife that lands way too close to home; a guy overwhelmed by his girlfriend’s marathon-level orgasm skills; and a couples’ night that detonates when one husband goes feral for the wrong person. Stefani and Ray bring their best-friend logic and deeply unlicensed insight— with empathy and honesty. Please don’t cite us in therapy. [Apothic Pinot Noir, 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.

From body odor to boundary issues, this week’s reading of the Dear Annie column is giving eau de despair. One writer’s begging HR to handle a fetid coworker, another’s stuck between her mother-in-law’s feuding daughters, and someone’s “service animal” story is pure fiction. The Biffs tackle it all with equal parts compassion, chaos, and questionable ethics." [Marchese di Borgosole 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.

This week, the Biffs celebrate 150 episodes by heading to Reddit’s messy courthouse - Am I The Asshole? - to judge three cases that range from petty to downright sociopathic. We’ve got a neighborly heist involving patio furniture and audacity, a revenge bridesmaid in a color rebellion, and a “death wasn’t a tragedy” hot take that’ll make you clutch your pearls. Moral clarity? Never heard of her. [Moët & Chandon Imperial Brut Champagne]

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] 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

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