Jesse Callans: Transitioning While Parenting Four Kids + Writing Ollie in Between

Jesse Callans: Transitioning While Parenting Four Kids + Writing Ollie in Between

Author: Jaimie Kelton – Queer Parenting & LGBTQ Families'. September 15, 2025 Duration: 55:00

Transmasc author and parent Jesse Callans joins Jaimie to flip the parenting script. Jesse shares how he pressed pause on transition to build a family (surprise—then three more!), what it looked like to transition while his kids were 7, 4, 2, and 1, and how toddlers helped distill a complex change down to “the things that stay the same” (yes, there will still be spoons and napkins). We dig into gendered expectations in public, the patronizing “wow, you’re so good with them” dad compliments, and why communal, queer-inspired parenting beats competition every time. Jesse’s middle-grade novel Ollie in Between tackles puberty, identity, and the gaps in sex ed—plus we talk book bans, hope in publishing, and why adults should read middle grade to hug their inner 12-year-old.


🏳️‍🌈 Key Takeaways

  • Transition with kids: rename “mommy” → Baba and center “things that stay the same” (routines, roles, rituals) to reduce anxiety.
  • Labels aren’t the hurdle—loss is: toddlers switch pronouns quickly; worries are about everyday continuity (the “spoons & napkins” moment).
  • Gendered bias whiplash: moms get judgment; dads get patronizing praise—either way, caregiving is undervalued.
  • Community > performance: open-door hangouts, shared labor, and imperfect playdates beat competitive, individualist parenting.
  • Paths aren’t linear: an unplanned start can still lead to intentional family and a later transition.
  • Middle grade matters: Ollie in Between fills puberty/identity and sex-ed gaps—adults should read MG to “hug your inner 12-year-old.”
  • Bans vs. demand: book challenges are real, but publishers and readers still want queer stories—keep requesting and buying.


🏳️‍🌈 About the Guest(s)🏳️‍🌈

Jesse Callans is a trans masculine author and father, known for his insightful writings that delve into gender identity and parenting. Having birthed four children, Jesse captures the complexities of family dynamics through a queer lens. His recent work includes the middle-grade novel "Ollie in Between," which addresses the challenging experiences of puberty from a perspective that champions inclusivity and understanding. Jesse resides near Philadelphia and uses his personal experiences to inform his engaging and meaningful stories.


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🏳️‍🌈 Resources Mentioned

  • Jesse’s book: Ollie in Between (Five One Friends/Macmillan) — find it at your local indie or wherever books are sold
  • Follow Jesse: Instagram @jesscallens
  • Newsletter: Get Jesse’s ongoing queer book recs — subscribe via QueerFamilyPodcast.com
  • Cruise with us: Spring Break April 2–6, 2026 to the Bahamas with Gays With Kids (Jaimie + family, José Rolón, Brian Rosenberg & lots of queer fams). Tell them Jaimie sent you.
  • Sponsor: California Cryobank — QUEERFAM25 = free Level 2 donor-catalog subscription (and a discount toward Level 3)


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Hosted by queer mom Jaimie Kelton, The Queer Family Podcast-LGBTQ Families & Queer Parenting Stories offers a weekly space that is both uproariously funny and deeply genuine. Each episode features conversations with LGBTQIA+ parents, hopeful parents, and their allies, delving into the specific joys and hurdles of building a family outside of traditional frameworks. You’ll hear firsthand accounts of the paths to parenthood-from adoption and fostering to IVF and surrogacy-and the everyday realities of raising kids in a world that can still feel unfamiliar. This podcast moves beyond theory, focusing on lived experiences that cover everything from health and fitness routines that work for queer families to navigating complex conversations about sexuality and society with children. The goal is straightforward: to share stories that normalize these experiences, elevate diverse voices, and celebrate the full spectrum of queer family life. Tuning in means connecting with a community, finding resonance in shared challenges, and gathering a lot of practical wisdom-and laughter-along the way. It’s a resource and a companion for anyone curious about or living within the beautifully expansive definition of a modern family.
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