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]

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 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.