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 2020 Cabernet Sauvignon]

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 2020 Cali Rose]

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 2108 Sauvignon Blanc-Chardonnay Blend]

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. [Villate 2020 Prosecco Rosé]

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 2013 Chardonnay]

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]

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 us your tan-lines. [Devils Backbone Vodka Mules]

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 2020 Sauvignon Blanc]

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 2020 Cotes de Provence Rose]

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]

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. [2019 Indomita Pinot Noir Rosé]

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 2017 White Blend]

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 Bay vs. White Haven - 2021 Sauvignon Blanc]

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]

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 2021 Sauvignon Blanc]

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 2017 Chardonnay]

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 2020 Sauvignon Blanc]

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 2019 Vouvray]

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. [Simi 2019 Chardonnay]

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, and join the BiFFs as they go through Thillist.com's In Bed with Gigi Engle. [Le Bocce 2016 Chianti Classico]