Love, Take Two

José Rolón and Jaimie Kelton
  • 4.7 (77)
  • SOCIETY & CULTURE
  • UPDATED WEEKLY

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.

Episodes

  1. 3D AGO

    Surviving Conversion Therapy: Timothy Schraeder Rodriguez on Faith, Identity, and Megachurch Secrets

    What happens when faith, identity, and healing intersect in the most unexpected ways? For this week's guest, Timothy Schraeder Rodriguez, that intersection became both his greatest struggle and his most powerful mission. In this episode of Love, Take Two, Timothy opens up about his decade-long experience with conversion therapy while working behind the scenes at some of the most influential evangelical megachurches in America. He shares the complex journey of reconciling his faith with his identity as a gay man, and how that internal conflict eventually led him to leave the church world entirely — only to find his way back on his own terms. After moving to New York City eight years ago to escape the evangelical world, Timothy has built a life centered on authenticity and service. He co-founded Church Clarity, an organization that helps LGBTQ+ individuals find affirming faith communities where they can practice their beliefs without shame or judgment. His work has garnered national attention from major outlets like TIME, NBC, and The Washington Post. Timothy discusses his path to sobriety, his transition from church work to tech, and how writing became a healing tool that led to his upcoming book, "Conversion Therapy Dropout: A Queer Story of Faith and Belonging" (releasing May 2026). Despite everything he's endured, Timothy still attends church...sometimes. This is an honest conversation about trauma, resilience, and the courage it takes to redefine what belonging means when the institutions you once served reject who you are. Key Takeaways: The reality of conversion therapy and its lasting impactHow faith and identity can coexist authenticallyThe process of healing from religious traumaHow he began conversion therapy at 19 years oldWhy sobriety became essential to Timothy's journeyHow his experience has effected his ability to date now as an out gay manIf this episode moves you, share it with someone who might need to hear that faith and identity don't have to be at war — and come connect with us on social! Connect with Us ⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠⁠⁠⁠⁠⁠Timothy Schraeder Rodriguez Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    48 min

  2. MAR 30

    Shuga Cain’s Story of Reinvention: From Corporate Life to RuPaul's Drag Race

    What does it take to completely reinvent your life? For this week’s guest, Jesus Martinez — known to many as RuPaul’s Drag Race fan favorite Shuga Cain — the answer was walking away from stability and choosing something far less certain, but far more true. In this episode of Love, Take Two, Jesus reflects on the decision to leave behind a six-figure corporate career to pursue drag full-time. He shares how stepping into Shuga Cain felt like the most natural choice he could make. Since appearing on RuPaul’s Drag Race Season 11, Shuga has built a multifaceted career spanning performance, touring, acting, and hosting her baking show Gimme Some Shuga. But the path to that life wasn’t linear, and it didn’t come without doubt. Jesus opens up about what it means to start over later in life, the role community and love have played in that transition, and how embracing risk can lead to unexpected clarity. Key Takeaways Jesus and Jaimie's experience as performers on the Disney cruise Reinventing yourself later in life and navigating uncertaintyHow Jesus became a drag queen and his first performanceThe impact of RuPaul’s Drag Race on Shuga’s careerWhat being a drag queen in New York was actually likeThe next phase of life Jesus is finding himself in How Jesus left corporate America for drag stardom If this episode resonates, share it with someone who needs a reminder that even the hardest chapters can become the beginning of something new — and come hang out with us on social! Connect with Us ⁠⁠⁠⁠⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠⁠⁠⁠⁠⁠Jesus Martinez Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    45 min

  3. MAR 23

    Dana Goldberg on Love, Queer Identity & Using Comedy to Heal

    What happens when humor becomes a tool for change? For this week’s guest, Dana Goldberg, comedy isn’t just about getting laughs, it’s about telling the truth, building connection, and making a real impact. In this episode of Love, Take Two, Dana reflects on the experiences that shaped her voice. From finding her footing in stand-up to becoming a comedian known for saying the things everyone’s thinking (but might be too afraid to say out loud). She shares how navigating identity, relationships, and the world around her influenced both her comedy and her perspective on love. Over the years, Dana has built a career that spans television appearances on major networks, performing on stages alongside cultural icons, and co-hosting the hit podcast The Daily Beans. But beyond the spotlight, she’s also used her platform to help raise over $70 million for causes including LGBTQ+ rights, women’s health, and HIV/AIDS awareness — proving that comedy can do more than entertain. Dana opens up about the role love and community have played in her journey, the lessons she’s learned from using her voice for something bigger than herself, and how humor can help us process even the heaviest moments. Key Takeaways How Dana blends comedy with activism to create real impact The role of humor in navigating identity and relationships How she turned her lost love into motivation to pursue comedy Her start into comedy as a high schooler Why laughter can be a powerful tool for connection and change If this episode resonates, share it with someone who needs a reminder that even the hardest chapters can become the beginning of something new — and come hang out with us on social! Connect with Us ⁠⁠⁠⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠⁠⁠⁠Dana Goldberg Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    49 min

  4. MAR 16

    Jonathan Gregg on Overcoming Toxic Masculinity & Redefining Manhood

    What does modern masculinity actually look like? For this week’s guest, Jonathan Gregg, it looks a lot like vulnerability, feeling secure in yourself, and a willingness to question the roles we’ve been taught to play. In this episode of Love, Take Two, Jonathan reflects on growing up in a conservative Southern environment and how those early experiences shaped his understanding of identity, relationships, and masculinity. From childhood expectations to adulthood friendships, he shares how questioning those norms helped him build a more expansive view of what it means to be a man. Jonathan’s career has taken him through theater, television, and digital media, appearing in projects like The Blacklist, Blindspot, and Hightown. But beyond acting, he’s become known for candid conversations about friendship, fatherhood, and the complicated ways masculinity shows up in everyday life. Jonathan opens up about the importance of emotionally honest friendships, how fatherhood has reshaped his perspective on love, and why expanding the definition of masculinity benefits everyone. Key Takeaways Growing up in the South and how it shaped Jonathan’s understanding of masculinity Why male friendship and emotional vulnerability matter The evolving conversation around masculinity and identity How fatherhood changed Jonathan’s perspective on love Navigating relationships while challenging traditional gender roles Why expanding masculinity creates space for deeper connection If this episode resonates, share it with someone who needs a reminder that even the hardest chapters can become the beginning of something new — and come hang out with us on social! Connect with Us ⁠⁠⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠⁠⁠⁠Jonathan Gregg Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    59 min

  5. MAR 9

    Sophie B. Hawkins: Love, Creativity & the Journey Behind Her Biggest Hits

    What happens when love, identity, and creativity collide? For this week’s guest, Sophie B. Hawkins, those forces have shaped both her life and her legendary music career. In this episode of Love, Take Two, Sophie reflects on the experiences that helped define her voice — from the early days of writing deeply personal songs to the breakout success of hits like “Damn, I Wish I Was Your Lover.” She shares how navigating identity, relationships, and the pressures of fame influenced both her artistry and her outlook on love. Over the years, Sophie has built a career defined by fearless honesty and emotional depth. Her music has resonated with listeners across generations, especially within the LGBTQ+ community, for its openness about desire, vulnerability, and authenticity. Sophie opens up about the role love has played in her creative process, the lessons she’s learned from motherhood, and how staying true to herself has guided her through decades in the spotlight. This is a thoughtful conversation about identity, connection, and what it really means to live authentically. Key Takeaways The inspiration behind Sophie’s iconic hit “Damn, I Wish I Was Your Lover” How identity and authenticity shaped her songwriting The role love and relationships play in creativity Lessons learned from decades in music and life How she used music as a way to heal trauma If this episode resonates, share it with someone who needs a reminder that even the hardest chapters can become the beginning of something new — and come hang out with us on social! Connect with Us ⁠⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠⁠Sophie B. Hawkins Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    55 min

  6. MAR 2

    How Jeremy Crittenden Turned a Difficult Chapter Into a Stand-Up Comeback

    We’ve all hit our own version of a rock bottom, right? Well, for this week’s guest, Jeremy Crittenden, that rock bottom moment became his take two. Known for his work in science fiction television, including roles on Star Trek: Discovery and The Expanse, Jeremy opens up about his unexpected journey into stand-up comedy, his experience performing on Broadway, and the deeply personal turning point that reshaped his life and career. What could have remained an extremely hard chapter instead became the catalyst for reinvention. Jeremy shares what it’s like to chase creative fulfillment across mediums — from scripted sci-fi to live comedy stages — and how humor became both a survival tool and a form of healing. This conversation dives into resilience, identity, risk-taking, and the courage it takes to pivot when life forces your hand.This is a story about reclaiming your narrative and turning your hardest moments into something unexpectedly amazing! Key Takeaways Jeremy’s leap into stand-up comedy and why it changed everythingThe Broadway chapter of his career Transforming an extremely difficult life moment into a true “take two.”Using humor as a tool for resilience and reinventionNavigating two divorces and what dating looks like for him now If this episode resonates, share it with someone who needs a reminder that even the hardest chapters can become the beginning of something new — and come hang out with us on social! Connect with Us ⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠ Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    43 min

  7. FEB 23

    Lena Hall on Kinky Boots, Hedwig & Winning a Tony Award

    What’s a childhood moment that quietly shaped who you became? For this week’s guest, Lena Hall, it was sending out invitations to her eighth birthday party and no one showed up. In this episode of Love, Take Two, Lena reflects on how her early experiences with performance, rejection, and identity influenced the trajectory of her career — both the drive that fueled her and the pressure that followed. That once self-described theater kid went on to become a Broadway powerhouse, appearing in major productions including 42nd Street, Tarzan, Dracula, and Kinky Boots, and later taking home a Tony Award. She’s also appeared in television series like Snowpiercer and Your Friends & Neighbors. But success didn’t come without cost. Lena opens up about the unexpected unhappiness she felt at the height of her Broadway career, her pivot into rock music, and how she has processed grief and personal loss through her work. Key Takeaways Growing up as theater kids — Lena and Jaimie reflect on their early years How childhood experiences shaped Lena’s career and creative identity The surprising emotional toll of Broadway success Pivoting from Broadway to rock music Processing grief and pain through performance Reclaiming joy after burnout If this episode resonates, share it with someone who needs a reminder that reinvention is possible and come hang out with us on social! Connect with Us ⁠⁠⁠Love, Take Two Instagram⁠⁠⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠⁠⁠Jose Rolon Instagram⁠ Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    1 hr

  8. FEB 16

    Missing Out Was a Win: Drew Droege on Life’s Second Acts

    We all thought we’d have it all figured out by 28… but what happens when not getting what you wanted turns out to be the best thing for you? In this week’s episode, Drew Droege shares candidly about missing the arbitrary goals he set for himself and how asking the question, “What does making it really mean?” completely changed his perspective.  Drew Droege is an actor, comedian, and writer best known for his viral Chloë Sevigny impressions and his work on shows like Key & Peele, Bob’s Burgers, and Reno 911! He’s also the creator of acclaimed off-Broadway shows, including Bright Colors and Bold Patterns and Messy White Gays, which recently ran in New York. Key Takeaways: Drew’s experience producing and working on Messy White Gays How can dark humor help process grief? Reflections on rejection and how it shaped his career The gut-wrenching experience of bombing a stand-up set Learning not to be precious about critiquing your own work Why Drew and Jaimie both hate Rent Connect with Us ⁠⁠Love, Take Two Instagram⁠⁠⁠⁠Love, Take Two Tiktok⁠⁠⁠⁠Love, Take Two Youtube⁠⁠⁠⁠Jaimie Kelton Instagram⁠⁠⁠⁠Jose Rolon Instagram Credits: Edited by: Jerson Barajas Recorded by: MCM Creative Produced by: Jose Rolon, Jaimie Kelton, and Dianni Hall

    41 min

  9. FEB 9

    Dominique Jackson on Pose, Activism, and Finding Her Power

    José Rolón and Jaimie Kelton sit down with the iconic Dominique Jackson — actress, model, and LGBTQ+ advocate best known for her role as Elektra on Pose — for a conversation about what a real take two looks like. Dominique opens up about her journey, from the debilitating fear she endured under the new administration as a trans woman to being brought back to life by her community. Together, they talk about Dominique’s experiences with domestic violence and her first marriage, what being on Pose was actually like, and the lessons she learned from it, and how she continues to take action as an activist for the trans and LGBTQ+ community. If you’ve ever wondered how Dominique Jackson became the icon she is today, you won’t want to miss this. Connect with Us ⁠Love, Take Two Instagram⁠⁠Love, Take Two Tiktok⁠⁠Love, Take Two Youtube⁠⁠Jaimie Kelton Instagram⁠⁠Jose Rolon Instagram

    1h 8m

  10. FEB 9

    Welcome to Your Second Act with Jaimie Kelton and José Rolón

    Welcome to Love, Take Two! In this solo kickoff episode, José Rolón and Jaimie Kelton share why they created this podcast and what “take two” really means to them. They open up about the moments that forced them to pivot — in love, in work, and in life — and why starting over isn’t failure, it’s information. Think less “perfect comeback story” and more honest reflections on detours, doubts, and choosing yourself when things don’t go the way you hoped. This is the beginning of a series of conversations about reinvention, resilience, and the weirdly beautiful process of trying again. Connect with Us Love, Take Two InstagramLove, Take Two TiktokLove, Take Two YoutubeJaimie Kelton InstagramJose Rolon Instagram

    47 min
  11. Love, Take Two - Official Trailer

    SEASON 1, EPISODE 1 TRAILER

    Love, Take Two - Official Trailer

    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.

    2 min

Trailer

4.7
out of 5
77 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
    2K
  • Episodes
    11
  • Rating
    Explicit
  • Copyright
    © José Rolón and Jaimie Kelton
  • Show Website
    Love, Take Two

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