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

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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🏳️‍🌈 Book with GWK's Spring Break Cruise Vacation! Join Jaimie and her family (and other LGBTQIA+ families) on a 3 night cruise in the Bahamas. Be sure to mention that you heard about it here! Click that link ➡️ https://travelbrilliant.net/mbg/gwk-spring-break-2026/

🏳️‍🌈 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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