Brian and Judson are joined by co-author of Dads and Daddies Book Club selection, Kink for Dummies, Jack Harrison-Quintana. Jack tells Brian and Judson how he first met and became close with his co-author Jaime M. Grant, and how the two came to write a book about kink for Wiley, publisher of the entire slate of For Dummies books. Jack shares his early kink origins on both personal and professional planes, he asks Judson about his history with kink and drugs, and discusses whether or not Brian’s affinity for group and public sex makes him a kinkster. Jack also explores whether or not kinks can exist without personal shame or judgement of the community at large, how the tenets of the kink community should be guiding principles for all of humanity, how couples can communicate about uneven kink desires, how not all kinks appear sexual, removing shame from the need for erectile dysfunction medication, and so much more. Jack then helps Brian and Judson respond to a Go Ask Your Dad question from a listener in a newly opened relationship who wants help finding sex parties, but also has concerns about safety and comfort with other attendees’ behavior.

Brian and Judson host their first podcast orgy of sorts with three repeat hookups at once! Adult entertainment stars Jonah Wheeler, Joel Someone and Daddy Kylex return to the basement to talk about all things pornography– their friendships, their working relationships and how they help one another navigate the industry. Joel and Kylex talk about what it’s like to be actual neighbors, and how it makes for some spontaneous content shoots. Kylex and Jonah talk about sharing partners, leadin gto unintentional continuity and Easter Eggs between their videos. Joel shares the story about how he brought Jonah into the business via a miscommunication that turned out to be a happy accident and grew into a proper mentorship. The three explain why the videos they make together are some of their favorite content, how romance, intimacy and even the L word figure into their sexual encounters, and share new Daddy Issues--two with app behavior, and one with the loss of vulnerability after taking on the Daddy role for so long. To close, the three help Brian and Judson respond to a Go Ask Your Dad question from a listener who wants to learn how to love his own body.

Brian and Judson are joined by comedian, actor, podcaster, musician, television writer and author of the new book, The Terrible, Horrible, No Good, Very Bad Gay, Eliot Glazer! Known to many for his performance as Eliot, brother to Ilana on the beloved TV series Broad City (and in real life), Eliot talks about how often he feels he’s a disaster as a gay man, and how his book is meant to provide others feeling the same way belly laughs and the comfort that they’re far from alone. He talks about how he copes with his anxiety as he searches for the perfect sex party, how he measures one’s gay age, his belief that his future husband exists in the midwest, the failings of gay sports leagues, his close relationship with his famous sister, and how the book provided the opportunity to separate himself from her and establish his own voice. He also tells Brian and Judson about the connection he made with a Gen Z hottie through their generational differences, and helps them respond to a Go Ask Your Dad question from a listener who is more newly out than his partner and wants to open their relationship so he can continue his sexual exploration, but doesn’t know that he will feel comfortable with his partner hooking up with other people.

Brian and Judson are overjoyed to welcome back to the studio, Dads and Daddies’ very own Dr. Daddy, Dr. Demetre Daskalakis, Chief Medical Officer at Callen-Lorde Community Health Center in New York City, a leader in LGBTQ+ healthcare both locally and nationally. Dr Demetre brings Brian and Judson up to speed on the developments in his life and career in the eight months since his prior appearance on the podcast, including a move from Atlanta to NYC, and taking on Callen-Lorde's medical leadership. He teaches Brian and Judson about syndemics (synergistic epidemics), what they mean for the queer community, and the initiative he introduced at Callen-Lorde to help LGBTQ+ people live their full lives in the safest ways possible. He also explains PrEP on demand, injectable PrEP, and the relationship between Undetectable and Untransmittable. He talks about Big Pharma and the queer community, and the less obvious reasons we need to make universal healthcare a reality in the United States. He also talks about his philosophy that self-care as LGBTQ+ people is the highest form of rebellion, and describes what self-care looks like for him, personally. To close, Dr. Demetre fulfills his promise and answers not one, but four medical Go Ask Your Dad questions that have been submitted since his first time on the show.

Brian and Judson are joined by Judson’s dear friend, star of Netflix’s “Owning Manhattan,” and the founder of Queerity — the world’s first sober LGBTQ+ social and lifestyle app — Jordan Hurt. Jordan takes them through his journey from his childhood as a self-described “punk rock kid from the gutter,” to his move to New York with little money and no prospects, to his time as a sex worker, to his incredible success as a real estate broker under the guidance of famed realtor Ryan Serhant. He goes into great detail about his sobriety journey, including his rock-bottom moment that played out in front of the cameras for the hit reality show he was a cast member on. He then tells them all about Queerity–how he came to develop it, and the ways in which sober people can use it to find friends, romance, sex, events and safe destinations. He also shares his renewed views on dating, romance and what the future may hold for his personal life. The episode ends with Jordan helping Brian and Judson respond to a Go Ask Your Dad question from a listener who wants help navigating a friendship with someone he is concerned is heading down a dangerous path with alcohol.

Brian and Judson are joined by the founder and CEO of the Daddyhunt app, Carl Sandler. Carl shares how Daddyhunt first came to be over twenty years ago and how it has evolved with the PrEP generation as the gay community has become more open to Daddies and to open relationships. He tells the story behind the Daddyhunt serial that became a viral sensation ten years ago, and talks about its upcoming re-release this year in 4K for a post-Heated Rivalry world. Carl helps Brian and Judson think about how gay men can and should behave better towards one another, explains what he as a Daddy gets from the younger men he surrounds himself with, discusses how Daddiness at its core is about giving back and what that looks like, delves deep into the importance and benefits of gay friendships, and he issues a life-and-death warning to all sons. To close, Carl helps Brian and Judson respond to a Go Ask Your Dad question from a listener who wants to know what it takes to be a good son or sub.

Brian and Judson are joined by podcaster and documentarian Jess Rothschild, creator and executive producer of the GLAAD Award-nominated docu-series Finding Fire Island, now in its second season—with many episodes featuring Judson! Jess tells Brian and Judson how she came to fall in love with Fire Island, why she felt it was important to document its deep history, and asks each host to share their Fire Island origin stories. She also shares her views on 12-step programs, explains how she is attracted to women but prefers the company of gay men, and discusses the differences in how lesbians and gay men approach sex and openness. Finally, Jess helps Brian and Judson respond to a "Go Ask Your Dad" question from a listener who has found a spark with someone online but is unsure whether or not he should remind this person that they interacted years earlier—and that it ended on a sour note.

Brian and Judson are joined by Emmy Award–winning writer, actor and comedian Bryan Safi! Bryan tells Brian and Judson all about his off-Broadway solo show, Are You Mad at Me?, his eight years so far on Ryan Murphy’s “9-1-1” alongside Angela Bassett, Peter Krause and Jennifer Love Hewitt, and his pioneering, near 15-year career as a podcaster. He details his obsession with grocery stores, compares notes with Brian and Judson on finding love while looking for sex online, shares the details about why his marriage ended in divorce, reveals his need for reassurance from someone in a position of authority, and talks about healing the long-contentious relationship with his conservative parents. The three also talk about some of their favorite celebs from the 80s and 90s like Joan Rivers, Mr. T, Britney Spears and both Jason Alexanders. Bryan then helps Brian and Judson respond to a Go Ask Your Dad question from a listener who is finding himself so horny that he can’t figure out how to satisfy his needs.

Brian and Judson are joined by the writer and performer Michael Musto called “Oscar Wilde meets Whoopi Goldberg,” Justin Elizabeth Sayre. Justin tells Brian and Judson about their new solo show they’re bringing to the Edinburgh Fringe Festival this summer, Justin Elizabeth Sayre is a 40 Year-Old Woman, how it was inspired by having to learn how to age as a queer person without role models to follow, and about the origins of their beloved Night of a Thousand Judys – an annual benefit for the Ali Forney Center, the nation's largest non-profit providing shelter and healthcare services to LGBTQ youth experiencing homelessness in New York City. Justin also talks about their journey to accepting their queerness, the on-and-off courtship via text and DM of their now wife, being a non-binary person married to a trans woman, and how the last presidential election forced them to expedite their wedding in the United States, before moving out of the country out of concern for their wife’s safety. Justin’s Daddy Issue sparks a debate about how to present oneself on the apps.

Brian and Judson are joined by global superstar - and a Grand Marshal of the 2026 New York City Pride March - Peppermint! An actress, singer, and comedian who rose to international fame on Season 9 of RuPaul's Drag Race and has become one of the most prominent voices in the fight for trans inclusion everywhere, Peppermint talks about the current barriers keeping trans people from living happy and healthy lives, why fighting for civil rights is a core part of her being, why she chose to audition for RuPaul's Drag Race, why her season wasn't appreciated at the time, the divisive Drag Race queen she admits is one of her favorites to tour with, and the extreme expense of drag competitions. She also details how she was required to audition for the role based on - and named for - her on Netflix's Survival of the Thickest, how she finds confidence through gratitude, her relationship with dating, what dating is like for trans women, and so much more.