Be A BiFF Media

Ill Advised with Stefani & Ray

Comedy EN ↓ 161 episodes

Peruse the advice columns over a glass of wine with Stefani and Ray. Listen on while they put years of therapy and life experience to the test against some the best columnists out there with their own comedic approach.

Author

Be A BiFF Media

Category

Comedy

Podcast website

illadvisedthepodcast.com

Latest episode

Jan 21, 2026

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Episodes

59 | Gaslighty 29.03.2023

The BiFFs go back to Ask Oloni of SimplyOloni.com this week. Topics include exposing an old flame to an STI in a non-consensual, monogamous relationship; convincing oneself to stay in a relationship because of your partner's mental health; apologizing to your man because of his insecurities; and what to do when oral sex isn't reciprocated. [A to Z Wineworks Bubbles Sparkling Rose] Send us your que...

58 | Hang On To Your Diapies 22.03.2023

This week, the BiFFs mix it up with Amy and Annie this episode, covering: an exes dark secret plaguing a Mom, a secret girl-friend of two years with a lover less than half his age, & a writer leaving an emotionally abusive relationship facing a moral obstacle. [VOGA Italia Pinot Grigio, 2021] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Fin...

57 | Side of Raunch 15.03.2023

This week, the BiFFs take to the Slate's "How To Do It" column to discuss a woman treating her husband's affair as personal entertainment, the ethics of removing a condom mid-sex, and the type of porn you might need to be watching to prove that you're straight. [Château Recougne Bordeaux Supérieur, 2018] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail....

56 | Utilize Your Urethra 08.03.2023

Reflecting on the NY Times’, the Ethicist, the BiFFs try their hand at providing moral and ethical guidance regarding a mother’s confession of infidelity following her husband’s death, a writer who wonders if the murder she witnessed is canon, and the ethical responsibility to reveal that the death of a son was due to an overdose. [La Marca Prosecco] Send us your questions, feedback, &/or wine...

55 | He Shan’t Advise 01.03.2023

The BiFFs talk through the guidance of Advice Goddess Amy Alkon. An unsupportive best friend isn’t your best friend. A husband trying to “show up” stirs up memories of hate and deceit. Paper thin walls allow a neighbor to eavesdrop on another’s verbal abuse. Girl’s night turns into a discussion about the value of “I’m sorry.” [Cloud No. 9 Sauvignon Blanc, 2017] Send us your questions, feedback, &a...

54 | Auntie AITA 22.02.2023

The BiFFs take to Reddit’s Am I the Asshole (AITA) thread. Topics include wall demolishing tongs, taking away your maid of honor’s “plus-three,” dirty underwear in exchange for groceries, and cutting out on your son’s wedding to be with his ex-wife. [Bodega Garzon Cabernet Franc, 2019] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/c...

53 | That’s Cough With An ’L’ 15.02.2023

Workplace wet dreams. Kids' similarities to their father trigger mom. Crazy ex-girlfriend gets ballsy. It gets personal with Little Village Mag’s Dear Kiki. All that and more from the Biffs in this week’s episode. [Mauro Molino Barbera d'Alba, 2020] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/credits for this and all of our episod...

Ill Advised w/ Stefani & Ray: Trailer (Extended) 09.02.2023
Ill Advised w/ Stefani & Ray: Trailer 09.02.2023
52 | Walking Bowel Syndrome 08.02.2023

The BiFFs revisit the Urban Diplomat this week. One writer teeters between shame and falling from grace. A peeper complains that her neighbor is peeping. Lemonade and ball-hockey piss off an abutting neighbor. And do ear infections really put hair on your chest? [Bancroft Estates Sauvignon Blanc, 2021] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.co...

51 | Part My Red Sea 01.02.2023

This week’s episode features Dear Kiki. The BiFFs discuss the dislike of receiving oral sex, a minor on Tinder pushing the legal limits with a twenty-three year old, and age as a factor in a relationship where the other half is barely legal. [Cap Royal Bordeaux Supérieur, 2019] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/credits f...

50 | Came Back With A Yamaka 25.01.2023

On the week of our 50th episode, we’re talking through the classic Dear Abby columns. A man keeps his knowledge of his wife’s affair from her. A father and daughter, each struggling with addiction, wage a child-custody battle. A dormant STI turns a long marriage into a ‘whodunnit.’ [Luc Belaire Gold Champagne] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@...

49 | It’s the Moistest 18.01.2023

Recorded in 2022, this weeks episode is call-back to advice column classics, Abby and Annie. A step mom demands modest panties at her wedding. A woman finds her engagement ring distasteful. A person in recovery wants to stay on track by saying goodbye to her former love. Finally, a wife catches her husband talking to other women on Twitter. [Apothic Pinot Noir] Send us your questions, feedback, &a...

48 | The Little Train That Can 11.01.2023

The BiFFs revisit the Slates “How To Do It” this week. High school sweethearts agree to open the relationship, but one loses their head. A wife shares her husband’s penile counterfeit with her bestie. And a girlfriend wants veto power when her man zeroes in on her friend. [Peirano Estates “The Immortal Zin” Zinfandel, 2016] Send us your questions, feedback, &/or wine recommendations to illadvi...

47 | Pullout’s Forever 04.01.2023

Happy 2023! The BiFFs kick off the New Year with a new column, Urban Diplomat - covering nude leaks on the internet, workplace porn, and bedside-rights. [Lilliano Chianti Classico, 2016] 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

46 | You Already Came 28.12.2022

In the last episode of 2022, the BiFFs get to the heart of family drama with Dear Abby’s Holiday advice throughout the years. [Absolut Peppar Bloody Mary] 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

45 | We Put the ”Ugh” in Thought 21.12.2022

The BiFFs help a spouse navigate the holidays with her own real-life Scrooge, weigh in on break-ups over the holiday season, and contemplate accepting gifts from those we perceive as less fortunate. [Marques de Caceres Garnacha, 2018] 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...

44 | Pass Me The Stiff Cheese 14.12.2022

It's bad advice all around this week. The BiFFs take on a Mom who wants to give her youngster a custom thong, a husband past his prime loves on his kiddos leaving his wife jealous, and a parent makes a big deal out of pronouns. [Antigal Uno Malbec, 2018] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/credits for this and all of our e...

43 | Swing-Bangin’ to Death 07.12.2022

A husband who won’t put out kills his wife’s vibe. Parents of forbidden lovers offer to end their love for them. Heather wants to blow her parent’s sexy swinging secret. [Valdo Rosé Brut] 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

42 | Momma Said Knock You Up 30.11.2022

This week the BiFFs play poison control with E. Jean, and then join Prudie to intervene in racial stereotypes and dodge an exorcism. [Austerity Cabernet Sauvignon, 2017] 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

41 | You Gon’ Give Thanks 23.11.2022

It’s Thanksgiving and the BiFFs are in the holiday spirit. Let’s serve up a side of unhelpful in-laws, with a little Black-Friday shopping poured over top. Who needs turkey when you can serve politics on a silver platter. Set a plate for Dad’s little secret. She’s coming to dinner, and she ain’t keeping quiet. [Sail to Trail Malbec, 2016] Send us your questions, feedback, &/or wine recommendat...

40 | Lordy, Lordy 16.11.2022

The BiFFs celebrate forty episodes with an audience of family and friends. Listen on as they tackle Reddit's Am I The Assh*ole thread. Join Stefani, Ray, and friends as they address a deadbeat fiancé, a live-in mom’s disrespect, a house-stealing brother, and a woman who chooses her partner via credit check and bank info. [Sterling Chardonnay, 2019 (White Sangria)] Send us your questions, feedback,...

39 | For Entertainment Purposes Only 09.11.2022

The BiFFs warm up with Gawking Gary and Sterile Steve, who hasn't put out for ten years. Oh, bee-tee-dubz, your mother puts out. [Old Soul Chardonnay, 2020] 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

38 | Rectum Ralph 02.11.2022

Stefani and Ray turn to the Slate's "How to Do It" for content this week. Where does Chelsea put her Cherry Chapstick? Mother and son - a bond to be undone. How hot is your cousin? Hot enough to...? It ain't a wine night. [Chateau Bel Air Bordeaux, 2019 & Bonfante & Chiarle 2015 Barolo, 2015] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com....

37 | I’ve Got A Sexy Sermon 26.10.2022

This week, Stefani and Ray reflect on Little Village Mag's Dear Kiki. A boyfriend falls victim to his girlfriend's trap when he accepts her invitation to rifle through her text messages. Rambunctious sexual responses from her partner leave a girlfriend's neighbors flustered. A friendly female finds herself dodging the advances of older men. [Château La Commanderie du Bardelet Sauvignon Blanc, 2018...

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