11. How We Prep Our Big Kids for Drop-Off Play Dates

In this episode, we normalize the worries and bloopers that can weigh on our minds as parents when we transition from “sittervising” our children’s playdates to that first drop-off. It’s a milestone that’s rarely talked about, yet can feel surprisingly big those first few times—whether you’re the hosting home or the one entrusting your child to someone else for a few hours.We candidly chat through:When we started noticing signs of readinessThe questions we prioritize when vetting for safetyThe conversations and social courtesies we encourage our children to practice when visiting someone else’s homeBecause here’s the thing: big kids can bring big energy. They’re still learning, still growing, and need space to stretch their independence—but within limits and guidance that help their “social play era” run smoothly. This is a must-listen if your child is 5+ and you’re right on the cusp of this next stage—when kids start widening their horizons and craving more peer play in non–adult-led settings.Show Notes:We are two moms who met on Instagram years ago and quickly bonded over our love of the Montessori philosophy applied to parenting and over nerdy child development research. We decided to take the leap by finally taking our chats out of our DMs and inviting you to listen along as we chat about all things motherhood.Gloria is a former 1st grade public school teacher turned work-from-home and now Montessori homeschooling mom to her 6 and 4.5 year old. She mentors parents on Montessori homeschooling online and has created multiple masterclasses for parents and educators on how to teach children to read at a foundational level. You can find more about her mentorship program by ⁠⁠clicking here⁠ ⁠and more about her masterclasses and other printables she has created for homeschoolers by ⁠⁠clicking here⁠. ⁠You can find her on Instagram ⁠@MontessoriMamaLife⁠Jenna is a mom of three, communications strategist and child development writer. With a bachelor’s degree in journalism and a specialization in sociology, she began her career in newsrooms and nonprofits before discovering her true calling in education. She partners with Montessori school teams to strengthen their outreach, refine family communications, and foster deeper connections between parents and educators. You can follow her musings on Instagram ⁠@holdingspacemontessori. ⁠