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Love, Take Two
Love, Take Two
Author: José Rolón and Jaimie Kelton
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© José Rolón and Jaimie Kelton
Description
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.
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.
33 Episodes
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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 TakeawaysWhy 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
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 TakeawaysHow 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.
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
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.
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 TakeawaysHow 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.




