Be A BiFF Media
Ill Advised with Stefani & Ray
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
Podcast website
Latest episode
Jan 21, 2026
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Episodes
36 | Rock Hard Chonkers 19.10.2022 1:14:45
Emily Yoffe of tried-and-true Dear Prudie fame takes center stage as the topic of conversation with Stefani and Ray. A live-in girlfriend takes it upon herself to surveil the kids. A husband's dead wife gets credit for making way for happiness in his new marriage. A trans woman keeps her transition a secret from her new partner. [Chateau de Roques Puisseguin St Emilion, 2015] Send us your question...
35 | Gaybelline All Over Your Wedding 12.10.2022 1:01:56
The BiFFs hit another Facebook Community this week with entries on AITA (Am I The A-Hole). One troll wonders if she can send her partner's child to her grandparents because she looks like his late wife. Another poster gets a worker fired for being too pretty at her wedding. The last question involves a boyfriend meeting up with his ex- in a vacant home and it's complicated. Who's the assh*le, now?...
34 | Gee! I Sure Hope This Plumbing Works 05.10.2022 1:02:59
The BiFFs jump around between advice columnists this week. Amy of Ask Amy publishes a question from someone who evokes talk of "girl code" when a guy connects with a friend of a woman who ghosted him. A Miss Manners writer questions the intentions of their partner's need to constantly correct them. Carolyn Hax's question deals with commitment when a writer dates in wait for the next best thing. [1...
33 | STFU & Be Happy 28.09.2022 1:10:35
In this episode, Stefani & Ray circle back to classic columnist, Carolyn Hax. A reader once highly criticized is now lavishly praised by her parents and can't find middle ground. Another is too busy waiting for a relapse than enjoying her partner's victories. The final reader questions loyalty when asked to have her untruthful partner's back. [19-Crimes Shiraz, 2021] Send us your questions, fe...
32 | Was Jesus Circumcised? 21.09.2022 54:13
This week, the BiFFs go back to basics with a 2010 Dear Abby column. A mature married man crushes on a younger colleague thirty-two years his junior. A husband who works part time asks his fully employed wife to take on a second job to secure their family financially. Mother dearest finds out daughter's boyfriend isn't Jewish because of what's in his pants. [19-Crimes Cabernet Sauvignon, 2020] Sen...
31 | Hoot Nanny 14.09.2022 1:08:21
The BiFFs veer from the traditional columnists and turn to the Relationship Rules page on Facebook. A man becomes upset with his girlfriend when she refuses to give up her bank account info for a game console. A woman scorned kicks her beau to the curb and wants to rush the healing process. Finally, how do you deal when your husband laughs at you every time you try to initiate intimacy? [19 Crimes...
30 | Should’ve Used That Labia 31.08.2022 1:11:43
When Advice Goddess Amy Alkon speaks, the BiFFs suck up the scientific evidence. A business man’s penchant for dating models comes into question when it’s used as a measure for success. An independent individual insists on living their life while their needy counterpart sulks. A snooping boyfriend reads his girlfriend’s journal, realizing she has feelings for another man. [Ashbourne Sauvignon Blan...
29 | Duct Tape Under Her Boob 24.08.2022 1:11:25
Freak in the sheets, #MeToo in the streets. Heather can’t see why her boyfriend needs to have sex in the dark. Peggy Sue and Lyle Jones wonder if their vanilla’s still hitting the spot. [Vallate Prosecco Rosé, 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.illadv...
28 | Thanks for Cleaning Up After Me 17.08.2022 1:13:06
This week the BiFFs travel through time. Ann Landers and her vintage posts commandeer this weeks’ topics. Stay-at-home-wife or sex worker? Sure. But what about cat-fish fiancé? [Cartlidge & Browne Chardonnay, 2013] 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.ill...
27 | Miscumceptions 10.08.2022 1:04:14
The BiFFs find a new column this week in Simply Oloni. The Rap Whisperer makes a cameo in Missionary. Herpes on deck. What now? And Young Wild & Free wonders if her previous zest for sex defines what’s next. [Josh Rose Prosecco] 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 no...
26 | Elders On My Berries 27.07.2022 1:18:20
This week, Stefani and Ray read questions for Paging Dr. NerdLove of doctornerdlove.com. A love-sick pup dwells when his ex- elects the nuclear option following their break. Platonic tactics, a gym membership, and a new wardrobe have a reader questioning why they’re regularly friend-zoned. A thirty-year-old aromantic virgin worries she’ll find her feels whilst living in her parent’s basement. Send...
25 | C is for Kinky 20.07.2022 1:31:08
This week's questions come from Thrillist's "In Bed with Gigi Engle." When a girl runs hot-and-cold, a man in denial worries he's hit the friend-zone. One reader worries that her kinks with her new beau might make her too 'whorey.' Another reader tortures themselves about their relationship status with a person who's more interested in their friend. [Allan Scott Sauvignon Blanc, 2020] Send us your...
24 | Douche Responsibly 13.07.2022 1:38:19
Dan Savage's "Savage Love" give the BiFFs some food for thought when a 19 year old girl asks for advice after a sexual partner insults her physique in bed. Can a hall pass go wrong if a hall pass don't pass hall? [Ninety Plus Cellars Cotes de Provence Rosé, 2020] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/credits for this and all...
23 | Toasted Toast 06.07.2022 1:10:39
The BiFFs take on Logan Hill of Cosmopolitan.com. Do boys talk in the potty? Cheating Chastity ponders a bachelorette party despite her boyfriend's concerns. Red Flag Rhonda's rose colored glasses render elusive second date. Taxi Tara's hook-ups leave her wondering if the problem is her boyfriend. [Chateau Haut Peyruguet Sauvignon] Send us your questions, feedback, &/or wine recommendations to...
22 | Dick, Thom, & Beelzebub 29.06.2022 1:17:19
The BiFFs revisit a favorite - Slate Magazine's Dear Prudence. A sex addict's partner questions her nieces motives with her new breasts. A sexless marriage entices one writer to ask how to have an affair. Meanwhile, a self proclaimed cuck-for-hire tells her mom about her side-hustle only for her professional life to be affected. [Indomita Pinot Noir Rosé, 2019] Send us your questions, feedback, &a...
21 | Testes, Testes, 1-2-3 22.06.2022 1:11:37
This weeks questions come from Ask E. Jean’s column of Elle Magazine. A spouse pits her future with her internet influencer counterpart against her biological clock. Another writer is ghosted and can’t accept that his decision is set in stone. Finally, how do you tell your children that they were at one point cryogenically stored? [Tenshen White Blend, 2017]
20 | Definitely in the Pants 15.06.2022 1:06:18
In honor of Pride month, the BiFFs take on S. Bear Bergman's "Ask Bear." A straight-identifying man looks for advice when he starts having feelings for his bro. Another writer worries that their friends are right and that they take themselves too seriously. The BiFFs also follow through with their promise for a wine tasting challenge. Winner asks the other BiFF whatever question they want. [Oyster...
19 | Seeked. Sought. Sucked. 08.06.2022 1:09:09
The BiFFs talk sex this week with Little Village Mag's Dear Kiki. Stefani redefines pegging when a reader asks about the prospect of penetrating her male partner. A swinging couple wants to broach the topic of having a mutual friend join them in bed. A man with a monthly hall pass can't quit what he hit. [Mezza Di Mezzacorona Extra Dry Rosé] Send us your questions, feedback, &/or wine recommen...
18 | Wick My Moisture 01.06.2022 1:34:02
The BiFFs take a stand against plastic surgery to please one's partner. A one night fling results in a pregnancy and a slew of unsupportive family members. Finally, should you drug your Mom, even when it's to her benefit, without her knowing? [White Haven Sauvignon Blanc, 2021] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find sources/credits f...
17 | You Can’t Do It Alone 25.05.2022 1:03:22
In the last episode in the Mental Health series, the BiFFs look back at how untreated mental health issues affected their families growing up, the influence that it has now being parents themselves, and how they plan to navigate that dynamic with their own children. [Sebastiani Chardonnay, 2017] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find...
16 | The Forest of My Life 18.05.2022 1:20:28
The BiFFs are reeling from a long, emotionally arduous day in the third episode of the mental health series. A series of events prior to recording guide an otherwise aloof pair in discussing their current mental states, their coping mechanisms, and how exhausting tending to your mental health can been. [Z Alexander Brown Sauvignon Blanc, 2020] Send us your questions, feedback, &/or wine recomm...
15 | My Perception of Normal 11.05.2022 1:20:53
In the second of four episodes in the mental health series, the BiFFs delve deeper into their mental health struggles. They go over what their anxieties and depression look like, how they've been affected by them, and how that's played out in their relationships. [Clos du Gaimont Vouvray, 2019] Send us your questions, feedback, &/or wine recommendations to illadvisedthepodcast@gmail.com. Find...
14 | You’re At Where You’re At & That’s Okay 04.05.2022 1:44:00
May is Mental Health Awareness Month and Stefani and Ray kick off the month discussing their own personal mental health struggles. The first in a series of four episodes, the BiFFs get candid about their diagnosed conditions and their ever-evolving journeys in their quest to remove the stigma to promote safe and open discussions in the realm of mental health. Let's breach the topic over a glass of...
13 | Swipe If You Want The Pipe 27.04.2022 1:10:24
A story of internet love and first-time physical intimacy cause the BiFFs to relive a dual-cat-fishing. In spite of her orgasms, a question of impotency drives a woman to ask for outside help. A man's tryst with his best friends ex, blinds him to her personal agenda. Serve up a double sausage pizza, pour a glass of your favorite Ashanti (Le Bocce Chianti Classico, 2016), and join the BiFFs as the...
12 | That Really Googles My Grundle 20.04.2022 1:14:21
How do you feel about your fiance seeing other naked bodies at a strip club? Does your sober sibling have the right to dictate how you live your life? Is the quality of your friendships dependent on the material things that you own? The BiFFs put their advice up against Elle Magazine's Ask Jean. #WhatTheElle [Casillero del Diablo Malbec, 2019] Send us your questions, feedback, &/or wine recomm...
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