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.

Brian and Judson are joined by founder and CEO of the iconic Nasty Pig fashion brand, David Lauterstein. David shares the concerns that are top of mind for him this Pride Month, expressing dismay about those within the queer community who police how out, proud, and loud LGBTQ+ folx express their visibility. He also shares his thoughts on Nasty Pig’s nomination in Las Culturistas’ Culture Awards this year and on the uproarious debate on Gay Twitter this past March about the appropriateness of wearing Nasty Pig to nice restaurants. He divulges exciting news for the company and updates Brian and Judson on what’s next for his 2024 memoir, Sodomy Gods. He also gets personal in revealing how his 33-year marriage works, what he’s learned through maintaining a relationship for so many years, and celebrates the queer community for making and living by its own rules. David gives a pep talk to his “fellow Daddy bottoms” who are feeling more invisible as they age, encouraging them to realize that there is a robust market for them. To end, David joins Brian and Judson in responding to a Go Ask Your Dad question from a listener who wants advice on inviting a friend he and his husband have been crushing on into the bedroom with them.

Brian and Judson are joined by Elliot Tuttle, writer and director of Blue Film, available on VOD Friday, June 12. Elliot talks about the various responses he has received to his universally lauded film about a night shared between a camboy and a pederast, and how the story came to him. Judson is inspired by Elliot to reflect on his own past relationships with older men when he was in middle and high school. Elliot also tells Brian and Judson about his path from child movie critic to filmmaker, and explains his belief that the current emphasis on “queer joy” is ruining the taste of gay people. Finally, he goes deep into his favorite topic—dating—and particularly how he’s found his way to having so much fun with it. The episode ends with a Go Ask Your Dad question from a Daddy in a college town who is having trouble finding men his own age, and inadvertently ends up becoming a father figure to the younger men he dates.

Judson and Brian celebrate the second anniversary of the podcast, the launch of Season Three, and the start of Pride Month! Judson spots two gay people at his new place of work and strategizes to befriend them both. Brian provides two theatre recommendations for Pride Month. Judson struggles with sleep issues. Brian shares an Instagram post sent his way that examines the question “Why are gay men so divided on open relationships?” The Hookup of the Week comes from a listener who gets to prove his versatility when a hot connection made while traveling spices up his vacation more than once during his stay. Brian and Judson then begin their Go Ask Your Dad Extravaganza answering five diverse listener questions. They first tackle one about open relationship rules, particularly around repeat hookups; the second asks each to describe their self-care routines; the third wants to know the etiquette around finding people on social media after meeting them at a sex party; the fourth is from a listener who is having trouble with his fiancé’s desire to open the relationship; and the fifth and final question comes from a listener in an open marriage whose Bipolar II disorder makes his libido unpredictable and wants help balancing saving his sexual energy for his husband with allowing himself freedom to have hookups.