Love, Take Two

José Rolón and Jaimie Kelton

What happens when life doesn’t go according to plan? You take it again. Love, Take Two is a conversation-driven podcast about second acts, fresh starts, and the unexpected turns that lead us to who we’re meant to become. Hosted by José Rolón and Jaimie Kelton, each episode dives into candid, funny, and deeply human stories of love, loss, pivots, and plot twists. From breakups to breakthroughs, Love, Take Two is about choosing yourself, rewriting the narrative, and proving that when it comes to life and love, sometimes the sequel is better than the original.

  1. 5d ago

    Darra Gordon on Second-Parent Adoption, Allyship and the Fight for Every Family

    Most people assume marriage equality settled the question of who counts as a parent. Darra Gordon wishes that were true. In this episode of Love, Take Two, hosted by José Rolón and Jaimie Kelton, the CEO of Family Equality explains why LGBTQ parents still have to adopt their own children, and how uneven state laws leave families exposed. Darra shares her own experience: after she gave birth, she and her wife had to go through the courts for a second-parent adoption, with home visits and letters vouching for a parent who had been raising her child from day one. Jaimie shares the birth certificate that listed her as the father, and the clerk who would not fix it without a marriage certificate while a newborn screamed in the background. José talks about what it took to close out his late husband’s estate without the right protections in place. Darra also takes us through her own Take Two. She came out later in life and began her nonprofit career at Hetrick-Martin Institute, spending fifteen years supporting some of the most vulnerable LGBTQ youth in the country. From there she moved to GLAAD to work on a national stage, and then to Family Equality, where she says every step she took finally made sense. It was the place where her personal life and her life’s work came together, from getting her kids to school in the morning to pushing legislation forward. The conversation moves from heavy to joyful and back again. Darra describes Family Week in Provincetown as the world she wants to see, where families who spend the year fighting for their rights gather in the sunshine. José admits he now refuses to book a wedding that weekend, and tells the story of the underwear party that taught him nobody is looking. The group talks about the annual gala, which raises nearly a quarter of the organization’s budget, and why it matters that it is a place where kids are welcome. Darra also speaks candidly about the attacks on trans youth, a sermon at an Atlanta church that reminded her there are more people for us than against us, and why allies can reach rooms that LGBTQ speakers cannot. She closes with the legacy she hopes to leave, including the John Lewis Every Child Deserves a Family Act, and a moment on the street when a stranger thanked her for helping save his family, with her son watching. This is a conversation about hope as something you do, not just something you feel, and what it takes to build the sequel when the stakes are your own family. Key Takeaways Why second-parent and confirmatory adoption still exist, and what Darra and her wife went through to be legal parents of their own childHow Darra went from fifteen years at Hetrick-Martin Institute to GLAAD to Family Equality, and why she calls it a callingWhat Family Week in Provincetown and the annual gala say about joy as part of the workWhy allies can move people who might tune out an LGBTQ voice, and how kids are already shutting down stigma on the playgroundPractical ways to help: share your story, donate, talk about it at the dinner table, push for Spirit Day at your school, and vote for pro-equality candidates

  2. Oct 19

    Michelle Rago on Protecting Her Peace, Going Home and Being Single by Choice

    Most people expect the glamorous career to be the whole story. Michelle Rago will tell you hers happened by accident. In this episode of Love, Take Two, hosted by José Rolón and Jaimie Kelton, the luxury wedding producer takes us back to the girl who got her working papers at 14, skipped college, moved to New York with no plan, and ended up producing events around the world. She gets honest about what it took to get there, including a floral design business that never made money and the moment she realized she was a producer at heart. At 62, Michelle is in what she calls her next chapter, and she built it with intention. She talks about leaving Manhattan to move back to the small New Jersey town she swore she would never return to, rebuilding her health after a brutal early menopause, and learning to protect her peace. She opens up about growing up as the daughter of a mother who went to Princeton and rewrote the rules, a father who stayed her mother’s best friend until the end, and what it meant to be a child of an alcoholic. She says the hard thing happened early, and it turned chaos into her superpower. Michelle also talks about being single by choice since the early 90s and not wanting children, and why she refuses to let anyone treat that as something missing. She explains why she believes loneliness is loneliness no matter what a life looks like on paper. She shares how Dolly Parton’s philosophy of changing the world within your own zip code pulled her into philanthropy, from fundraising for her local library to a diaper and formula drive at her home, and how she’s now diversifying with a scripted series, a podcast idea, and another book. José and Jaimie join in with their own stories about friendships, boundaries, and what second chances look like at 50. This is a conversation about intention, independence, and what happens when you stop apologizing for a life that does not fit anyone else’s picture. Key Takeaways How a woman with no plan and no college degree became one of the top destination event producers in the industryWhat early menopause, a move home, and a stylist taught Michelle about rebuilding her health and confidence in her 60sWhy she says “the hard thing happened early” and how growing up with chaos became a professional superpowerWhat being single and childfree by choice has actually felt like, and why she doesn’t believe she’s missing anythingHow she circles the wagons, spots her ride or dies, and puts her energy into giving back within her own zip codeIf this episode resonated, send it to someone who needs a reminder that a life outside the box can still be full. Come hang out with us on social.

  3. Oct 12

    Demi Schweers on MS, Infertility and Sharing the Hard Stuff Online

    Most people think a second act starts after the hard part is over. Demi Schweers started hers in the middle of it. In this episode of Love, Take Two, hosted by José Rolón and Jaimie Kelton, Demi takes us back to 2020: a pandemic wedding in August, an MS diagnosis shortly after, and a conversation with her brand new husband, Tom, where she offered him a way out. He laughed at her and said no. That moment set the tone for everything that came next.Demi talks about losing her vision and the use of the right side of her body, a year of negative tests, a miscarriage, an emergency surgery for an ectopic pregnancy, and the doctors who kept telling her everything looked fine. She shares how a new clinic caught a PCOS diagnosis on the very first call, something no one had ever told her. Jaimie opens up about her own years of unexplained infertility and a recent endometriosis diagnosis, and the three of them get real about what it means to be a woman who has to fight to be heard in a doctor's office.She also gets into the decision to start sharing her story online, why she never hesitated once she realized one in four pregnancies ends in loss and almost no one was talking about it, and the little phrase that carried her through: one day closer. From there, Demi walks through the IVF process, the birth of Nora, her double rainbow baby, and the surprise of Teddy, whose pregnancy brought its own set of fears. She and Tom made an early choice to keep their kids offline, and José shares the story of meeting Demi at the White House.Demi also talks about leaving a sales career she could no longer physically do, betting on social media, and the business she built with a friend after spending hundreds of dollars a month trying to support her own hormonal health. Through all of it, she says the thread has stayed the same since her days as a teacher: if she can make a difference in one person's life, she has done her job.This is a conversation about slowing down, telling the truth, and what happens when you stop waiting for the hard part to end before you start living.Key Takeaways:-What Demi said to Tom after her MS diagnosis, and why his answer still means so much to her-Why "one day closer" became her way of getting through infertility, loss, and IVF-The moment she realized no one was talking about miscarriage, and why she decided to be the one who would-How being told "everything looks fine" delayed her PCOS diagnosis, and what José and Jaimie share about their own families' experiences-Why she and Tom chose to keep Nora and Teddy offline, and how she found a new career when her body could no longer handle the old one

  4. Oct 5

    Jose and Jaimie (and Dolly!) on Letting Your Light Shine, Dating at 50 and Navigating Co-Parenting

    Most episodes of Love, Take Two end with someone else's story. This time, hosts José Rolón and Jaimie Kelton turn the mic on themselves. The conversation starts with Dolly Parton's death, which hit Jaimie harder than either of them expected, cracking open old childhood memories and a quiet, long buried dream of singing in public instead of just dancing for the camera. What follows is a looser, more personal episode, less interview and more check in, as Jose and Jaimie talk through what almost two seasons of guests have actually taught them.They get into turning 50, and almost 50, and the strange experience of being told by a woman at the gym that she assumed Jose was decades younger. Jose opens up about Thomas, his parter who has shared his home for three and a half years now, what it's actually been like learning to share space and routines after a decade of doing things entirely on his own terms, and how having that support is the only reason this podcast exists at all. Jaimie talks about raising her kids in New York City with her wife Ann, the tradeoffs of city parenting versus what their guest Alexis described, and why, challenges and all, she wouldn't trade it.Woven through all of it is the throughline they keep noticing in guest after guest: Anthony Luciano starting over in his sixties, Jeff Hiller pushing past the shame of still chasing a dream in his forties, their youngest guest Alessandra proving it's never too late at any age. As Jaimie puts it, the lesson is always the same. People stop holding themselves back, and then they just do the thing.This is a conversation about what two people who ask everyone else about their second acts have learned about their own, and what happens when you finally let your own light shine instead of just shining it on others.Key Takeaways- What Dolly Parton's death unlocked for Jaimie, and the dream it's pushing her to finally pursue- Jose's reflections on bringing Thomas into his home and learning to share a life after a decade on his own- The real tradeoffs of raising kids in New York City, and why Jaimie wouldn't trade it despite the challenges- The throughline Jose and Jaimie keep noticing across guests like Anthony Luciano, Jeff Hiller and Alessandra- Why both hosts believe the real lesson of every Take 2 story is simple: stop holding back and just do the thingIf this episode resonated, send it to a friend who needs a reminder that it's never too late to finally do the thing you've been holding back. Come hang out with us on social.

  5. Sep 28

    Margaret Cho on Struggling, Sexual Assault in the Seventies and Sobriety

    Most people think reinvention means becoming someone new. Margaret Cho found hers by finally becoming fully herself. In this episode of Love, Take Two, hosted by José Rolón and Jaimie Kelton, Margaret takes listeners through the version of her story that rarely makes the highlight reel: leaving high school before finishing, chasing comedy and independence on her own terms, and landing a role that made television history as the star of the first Asian American sitcom, only to watch the network try to reshape her body, her identity, and everything that made her Margaret in the first place. She talks candidly about what that pressure did to her, the eating disorder it left behind, and the years of addiction, anxiety, and depression that followed as she tried to survive fame without a roadmap for how to do it. Margaret gets into what actually changed. Not a single dramatic turning point, but a decision to get sober, one she has now sustained for ten years, and the community and clarity that decision gave her back. She also opens up about her father, a Korean immigrant who felt invisible in 1960s San Francisco until he found the city's gay community and eventually opened a gay bookstore of his own, and about growing up as one of the only visible queer voices on television during the height of the AIDS crisis, a fact that becomes deeply personal in this conversation as José shares his own memory of watching her on TV as a teenager while his family navigated losing his father to AIDS in silence. Margaret also speaks directly about her advocacy for the trans community today, why she has no interest in softening that stance, and what it means to reclaim a label being used as an insult. This is a conversation about reclamation, resilience, and what happens when a decade of sobriety finally lets someone come home to themselves. Key Takeaways How network television tried to reshape Margaret during All-American Girl, and the toll that took on her body and identityWhat a decade of sobriety has given her that fame and success never couldThe story of her father's gay bookstore in 1960s San Francisco, and what it meant for him to finally be seenJosé's personal reflection on watching Margaret on television as a teenager while his family hid his father's AIDS diagnosisWhy Margaret refuses to back down from being called a "radical trans activist," and what she believes comedy's role is in the fight aheadIf this episode resonated, send it to someone who needs a reminder that surviving your past and thriving in your present are not the same thing, and that the second one is always still possible. Come hang out with us on social.

  6. Sep 21

    Alexis Kristiana on Texas, Toddlers and Trading the Suburbs for the City

    Most people think a second act means starting over somewhere new. Alexis Kristiana found hers by going back to where she started. In this episode of Love, Take Two, Alexis takes us through the version of reinvention nobody expects: leaving New York for a house in the Texas suburbs with her husband and three kids, doing everything she was told a good parent is supposed to do, and realizing somewhere along the way that it was the wrong life wearing the right furniture. She talks about the backyard nobody used enough, the son who cried in the car every day because he missed walking, and the moment she watched him get quietly, wrongly labeled before he'd even started kindergarten.Alexis gets into what it actually took to admit the move wasn't working, without treating it like a failure at all. No dramatic breakdown, no five year plan. Just three non-negotiables, a new one bedroom, three bedroom apartment ten minutes from where they used to live, and a decision to raise her kids in the noise and chaos she grew up believing you were supposed to escape. She opens up about becoming a mother in isolation during the pandemic, the videos her own mother recorded from across the world while stationed in the Navy, and how becoming a parent herself finally taught her what those recordings actually meant.For Alexis, going back wasn't retreat. It was proof that the life she wanted had been right the first time, she just had to leave it to find that out.This is a conversation about permission, homecoming, and what happens when you stop measuring a good life by the size of the house it comes in.Key Takeaways:-Why the backyard and the bigger house never solved the thing she thought they would-What her son's quiet withdrawal in the suburbs taught her about what he actually needed-The illegal, biased assessment that pushed her into homeschooling, and why she has no regrets-What her mother's recorded bedtime stories from the Navy taught her about presence, decades later-Why she believes the best second act isn't a leap forward. It's the courage to turn back aroundIf this episode resonated, send it to someone who needs a reminder that going home isn't giving up. Sometimes it's the bravest reinvention there is. Come hang out with us on social.

  7. Sep 14

    Lori E. Seid on Baby Dykes, Blue Men and Being in the Spotlight

    Most people think finding the spotlight means chasing it. Lori E. Seid spent 40 years actively avoiding it, and somehow ended up more essential to New York's downtown arts scene than almost anyone with their name on the marquee. In this episode of Love, Take Two, Lori takes us through the version of a career nobody plans for on purpose: starting out at a copy shop on West 8th Street making posters for broke, brilliant artists, and just never leaving. What followed was four decades of being the person everyone in the room trusted, road managing Sophie B. Hawkins before she'd released a single song, producing for Rosie O'Donnell's talk show, and turning down Blue Man Group's first millions because eight shows a week just wasn't her cup of tea. She talks candidly about coming of age as a baby dyke on Long Island in the 1970s, getting shipped off to Provincetown after her parents read her diary, and how the queer community there effectively raised her. She gets into the AIDS crisis with unflinching honesty, the lesbian safe sex handbooks she helped smuggle across borders, and the friends she lost who never got the chance to have a Take Two at all. Lori gets into what it actually took to finally step into her own spotlight, at an age when most people are told it's too late to start. No rebrand, no reinvention plan. Just a lifetime of material sitting in her tiny, forty-year apartment, and a night on stage that turned into the performance of her life. She opens up about the moment Cyndi Lauper stopped a nervous young singer mid-performance to tell her she belonged there, and how that memory cracked something open in Lori on the subway ride home. For Lori, this chapter isn't about becoming someone new. It's about finally telling the stories she's been collecting, on purpose, her whole life. This is a conversation about loyalty, timing, and what happens when the person who spent decades making everyone else look good finally decides it's her turn. Key Takeaways How a copy shop job on West 8th Street turned into a 40 year career working alongside Rosie O'Donnell, Cyndi Lauper, and Sophie HawkinsWhy she turned down Blue Man Group's early success, and how she felt about it laterWhat coming out on Long Island in the 1970s and being taken in by Provincetown's queer community taught her about survivalThe lesbian safe sex handbooks she helped create and distribute during the AIDS crisis, and the friends she lostWhy she waited until now, decades into her career, to finally step into her own spotlight If this episode resonated, send it to someone who's still waiting for the "right time" to tell their own story. Sometimes forty years of being everyone else's biggest supporter is exactly what gets you ready. Come hang out with us on social.

  8. Sep 8

    Anthony Luciano on Failure, Family Traditions and His Fashion Empire

    Most people think reinvention has to be a leap into the unknown. Anthony Luciano found his by doing the opposite. He just followed the current. In this episode of Love, Take Two, Anthony takes us through the version of success nobody puts on a mood board: getting fired three times from fashion jobs in his twenties, stitching costumes in the belly of a cruise ship for five years, and finally walking away from a design director job with no plan except to start making bags in his apartment the next morning. What followed was two decades of hand building a luxury handbag business from scratch. He landed in Bergdorf's and Neiman Marcus, all before the industry itself pulled the floor out from under him. He talks about watching retail collapse around him well before the pandemic finished the job, and the moment he realized he would rather close his own business than go work for someone else again. Anthony gets into what it actually took to rebuild, without treating it like a rebuild at all. No dramatic pivot, no five year plan. Just workshops in his studio one night a week that a Today Show segment turned into Sip and Stitch, the leather and wine experience that's now filled with strangers, celebrities, and his own extended family of regulars. He opens up about growing up the son of a carpenter and a homemaker in a small upstate New York town, watching his mother and grandmother sew and embroider by hand, and the tradition his late father kept alive for him: collecting pennies from the whole town so Anthony could put one into every bag he ever made, for luck. For Anthony, turning 60 didn't feel like an ending. It felt like proof that you don't have to fight your way upstream to end up exactly where you're supposed to be. This is a conversation about freedom, patience, and what happens when you stop treating a second act like it has to be a reinvention at all. Key Takeaways How getting fired three times in the fashion industry became the redirection that mattered mostWhat five years of costuming cruise ships taught him about freedom over securityThe Today Show segment that turned a one night a week workshop into a full business overnightThe penny his father collected from an entire town, and why every bag still carries oneWhy he believes the best second act isn't a leap. It's following the current you're already in If this episode resonated, send it to someone who needs a reminder that reinvention doesn't have to look like a comeback. Sometimes it just looks like paying attention to where you're already headed. Come hang out with us on social.

See All (33)

Trailer

4.6
out of 5
87 Ratings

About

What happens when life doesn’t go according to plan? You take it again. Love, Take Two is a conversation-driven podcast about second acts, fresh starts, and the unexpected turns that lead us to who we’re meant to become. Hosted by José Rolón and Jaimie Kelton, each episode dives into candid, funny, and deeply human stories of love, loss, pivots, and plot twists. From breakups to breakthroughs, Love, Take Two is about choosing yourself, rewriting the narrative, and proving that when it comes to life and love, sometimes the sequel is better than the original.

Information

  • Creator
    José Rolón and Jaimie Kelton
  • Years Active
    2026
  • Episodes
    33
  • Rating
    Explicit
  • Copyright
    © José Rolón and Jaimie Kelton
  • Show Website
    Love, Take Two

You Might Also Like