

Episode 139 | From Training Wheels to Hamster Wheel
A disappearing best friend who still lurks in case she needs something. A guy who shoots his shot via BCC. And a man losing sleep because his girlfriend’s on OnlyFans. This week, the Biffs dig into three very relatable modern-day dilemmas pulled from Love Letters: the blurred line between ghosting and passive-aggressive friendship, the wild west of digital dating etiquette, and the fragile male ego in the face of empowered women. As always, Stefani and Ray bring wine-soaked wisdom, chaos-calibrated advice, and zero qualifications—just the way you like it. [Bottlerocket Spritz, Sparkling Rosé]

Episode 138 | Self-Absorbed Succubus
This week’s mess includes backne, breakups, and body lotion masquerading as soap. Stefani and Ray dive into four gloriously messy AITA questions: the woman who asked her sister-in-law to sunscreen her bacne, the girlfriend who gave her boyfriend the crop treatment (literally), the almost-stalker who let a stranger cry it out, and the man who’s been washing his hands with body lotion for three weeks straight.
After listening to these blunders, one thing will be clear: some people simply shouldn't be trusted with a photo app or a pump bottle. [Summer Garden Spritz w/ La Marca Prosecco]

Episode 137 | Rotten Rhonda
Love is hard. Boundaries are harder. And your boyfriend’s about to cry again. This week, the Biffs dive into three emotionally chaotic conundrums: what to do when the dating drought has you questioning if marriage is even in the cards, how to end things with your boyfriend without emotionally wrecking him, and how to draw the line with your dad’s new wife without blowing up the family group chat. Stefani and Ray bring their signature, emotionally honest (and very unlicensed) advice to the romantically bewildered and boundary-confused. [Enrico Serafino Grifo del Quartaro Gavi di Gavi, 2021]

Episode 136 | You’re Gon’ Get This Deck
A psychic says dump him—so should she? This week, the Biffs dive into three very modern meltdowns, from The Independent's Dear Vix Column. trusting tarot over your own intuition, obsessing over your boyfriend’s ex (oops), and losing a friend to her walking red flag of a man. Stefani and Ray bring their signature best-friend banter and wine-fueled wisdom to the mess, offering emotionally honest (and very unlicensed) advice to the romantically bewildered. [Shimmer Francis Coppola Diamond Collection Sauvignon Blanc & Pinot Grigio Blend, 2024]

Episode 135 | Such Many Mouthfuls
This Biffs read from R. Eric Thomas’s advice column this week. A writer’s distrust in their second husband has them questioning if they should contact the first wife to get their real story. Another writer's sister-in-law loads up her car with her own thoughts of her inheritance following their parent’s death. Finally, tensions run high when a man’s one night stand resurfaces after forty-three years, shacking up with his brother. [Octopoda Prosecco]

Episode 134 | Exuberantly Flamboyant
This week, the Biffs read from Natalie Bencivenga’s Ask Natalie. What’s the correct course of action when your husband’s empowered to be more controlling as a result of the presidential election? Oldest friend may not mean best friend, but should you still help plan their birthday? Pregnant, and now your abusive boyfriend wants to get married? [Natale Verga Gavi, 2023]

Episode 133 | Curtsy, Bow, & Gyrate
After a ten-month hiatus, your Biffs are back! Stefani and Ray hit the waves refreshed with new questions and the same banter. This week, the Biffs take on the Slate’s “How To Do It.” A girl know’s too much about a new girlfriend’s boyfriend’s past, and is chomping at the bit to tell her. A man is turned on when he finds out his boyfriend is married, and wants to look the other way. A man’s fetish for golden showers is anything but when his wife is unsatisfied with the only way he wants to have sex. [Miguels Rosé]

Episode 132 | A British Southerner From Canada
Stefani and Ray visit Susan Writer's column, Ask Someone Else's Mom, this week. The Biffs read about potentially rigged, by-chance encounters with former flames; an inter-familial rivalry that has two uteruses vying for first; and a long-distance open relationship without rules on track for marriage. [Patrice Grasset Vin de France 2021 Chenin Blanc]

Episode 131 | Best of the Biffs (Part VII)
In this week's episode, relive some of the Biffs' favorite moments of Ill Advised. From episode 78 - How to Kidnap Us, a man's self-proclaimed stupid face is putting his wife off to sex with him. In episode 11 - God Damn It, Kourtney, her partner's weight gain has a woman questioning the future of her relationship. And from Episode 22 - Dick, Thom, & Beelzebub, a woman's lackluster sex life leaves her wondering if she can have extramarital affairs while staying with her husband.

Episode 130 | I Can Pretend it’s a Manhole
Out of the Vault: This week, the Biffs bring you an episode with unaired segments from previous recordings. From Reddit’s AITA, a father wonders if laughing at his son’s self-sabotage makes him an asshole. From Metro.co.uk, a man promises to suppress his homoseuality in exchange for shelter with his wife and their children. And from Ask Amy, a woman starts a Facebook dating profile after her husband does, but is asked to shut it down when she receives more attention.

Episode 129 | Besties Use Your Vibrators
In this week’s episode, the Biffs read from one of their favorite columns - Natalie Bencivenga’s, Ask Natalie. A series of unfortunate events in a contentious relationship leaves a grieving widow wanting to sever ties with her late husband’s son. A writer’s roommate-turned-close-friend crosses an unspoken boundary and violates her privacy when she borrow’s her sex toy. Another writer’s emotional capacity to handle her best friend’s grief fuels an interesting discussion between Stefani and Ray. [Stefano di Blasi 2021 Zibibbo Catarratto]

Episode 128 | Get Rich’d Down
Stefani and Ray attempt to weigh in on questions sent to the Slate.com’s How To Do It Column, by Rich Juzwiak and Jessica Stoya. A coupled individual’s want to connect intimately with girlfriends is interrupted by booty calls and one-nighters. Another writer’s realization that they’re non-binary, along with their penchant for masochism, leaves them wondering if their husband is the one for them. Finally, a woman’s attempt at back-door, dildo play activates her gag reflex. [Benjamin Darnault 2022 Grenache Gris Plus]

Episode 127 | We Are the Kool-Aid That Others Drink
This week, the Biffs revisit Reddit’s Am I the Assh*le (AITA) thread. A man’s disagreement with his wife’s unusual punishment of their underaged drunk son stalls communications at home. Another father questions whether he’s asshole for kicking his son out, when it’s revealed that he’s been staying with them because he cheated on his pregnant, bed-ridden wife. And a man’s dash cam footage reveals what he really did to the family dog. [Yalumba Y-Series 2022 Viognier]

Episode 126 | Throw Some Cheese on that, Bitch
The Biffs, Stefani and Ray, put new columnist, R. Eric Thomas of Asking Eric (Washington Post), to the test. He’s got big shoes to fill as he steps in following Amy’s (Ask Amy) departure. An anti-gay rights in-law puts together a family tree and leaves the writer’s husband of ten years out, because of her stance on same-sex marriage. A man who enjoys just about everything in his marriage can’t stomach another one of his wife’s home cooked meals. Finally, a DNA test has a sister questioning a moral dilemma: remaining loyal to her brother, or making herself known to his secret, estranged love child. [Chris Baker 2022 Willamette Valley Rose]

Episode 125 | Ass First. Adult Later.
The Biffs celebrate twenty-one years of Ask Amy with a send-off/tribute, including some of her best advice to date. Amy gets pranked in our first question, when a writer's scenario is the movie plot of the 2003 cult-classic, The Room. The second writer is a woman whose unchecked privilege, along with that of her family/friend group, gets in the way of her being a good sister. Finally, a dinner guest is upset following a party where the hostess fails to disclose that one of her guests was transitioning. [Beringer Bros. 2022 Bourbon Barrel Aged Chardonnay]

Episode 124 | Say Uncle & I’ll Stop
This Biffs read through Laura Collins's column in the Metro.co.uk this week. One writer asks for guidance on coming out to her mother about sleeping with her uncle. Another questions that status of his marriage when his postpartum wife cheats on him, following his unplanned vacation with his friends. And finally, a young man, sexually harassed by his dad's young girlfriend, doesn't know how to tell him. [Prophesy 2022 Rose]

Episode 123 | McMuff Me
In this week’s episode of Ill Advised, Stefani and Ray read from Miss Manners column from UExpress. One writer asks for help in determining when to relate and when to express empathy when someone close is sharing a personal problem. Another writer takes a tumble and becomes the joke of the friend group. Finally, a change in a cancer survivors appearance has them wondering how to redirect compliments. [Chateau Laborde 2018 Sauvignon Blanc]

Episode 122 | Best of the Biffs (Part VI)
It's another trip down memory lane as we relive some our favorite advice columns from our early days. From episode 13 - Swipe if You Want the Pipe, the Biffs address a writer's plan to get down and dirty with an internet beau. A man's uncut member becomes a Jewish mother's biggest worry, in episode 32 - Was Jesus Circumcised. And from Episode 72 - In the Privacy of Your Public, should Mom have knocked when the son uncharacteristically used the vacuum?

Episode 121 | Peen or Not?
Coleen Nolan, the Mirror.co.uk's agony aunt's column, is the topic of this week’s conversation between the Biffs. A woman’s insecurities over the life her daughter lives prompts her question to Coleen. Another woman’s husband doesn’t like it when she’s barefoot on vacation, when she just wants to air out the puppies. Finally, when your Biff doesn’t like your significant other, which side of the fence do you play on? [Aperol Spritz]
Find sources/credits for this and all of our episodes in our show notes at www.illadvisedthepodcast.com

Episode 120 | Little Piece of Pork Rind
The Biff’s read through advice from Jenee Desmond-Harris of the Slate’s Dear Prudence, this week. A woman finds her husband’s notes to himself on the best way to handle her in several scenarios. A husband cheats on his wife with the person she has a restraining order on, and now she’s ready to give notice at their co-owned business. Lastly, when the rat-tail when out of style, this writer thinks their baby book should’ve gone with it. [2022 J Vineyards & Winery Sauvignon Blanc]