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.