All Episodes

June 7, 2025 19 mins

In this tender and deeply honest episode, Jill and Bobby revisit one of the most emotionally loaded questions new parents often face: “Why don’t I feel connected to my baby yet?” Drawing from a personal excerpt in Jill’s book Mama Outspoken, they open up about the fear, grief, and self-doubt that came with not bonding during pregnancy, and how postpartum experiences didn’t immediately “fix” it. Together, they explore the emotional weight of unmet expectations, the unpredictable nature of birth, and the surprising ways bonding can eventually bloom. Whether you're a parent who's been there or someone supporting one—you’ll leave this episode feeling a little less alone.

In This Episode, You’ll Learn:

  • Why not bonding during pregnancy is more common than we talk about
  • How Jill’s cesarean birth and breastfeeding challenges shaped her early connection
  • The role of COVID isolation and grief in shaping maternal expectations
  • Bobby’s reflections on supporting Jill through her doubts and fears
  • The emotional pivot from fear of not bonding to being “too bonded”

If you've ever questioned your bond with your baby or wrestled with the pressure to feel a certain way in motherhood—this conversation is for you. Jill and Bobby remind us that connection isn't always instant, and that's okay. Healing happens in layers, and no two journeys look the same. Whether you're in the thick of postpartum or reflecting back, this episode is a powerful permission slip to let go of timelines and lean into grace.

💛 Join Team Mama Outspoken for the Hope is Here 5K! 💛

This June 21st, I'm lacing up my sneakers—not because I’m a runner, but because I believe no mom should walk through postpartum struggles alone. The Hope is Here 5K supports the Postpartum Resource Center of New York, an organization that’s been part of my story and a lifeline for so many families.  

Whether you’re a parent, partner, friend, or supporter, you can make a difference:  
👟 Walk or run with us in-person. Register here https://postpartumny.org/25hope/  
🤝 Donate to support moms in need here https://www.zeffy.com/team/mama-outspoken  
📣 Share this message to help spread hope Every step, every dollar, every share matters.  
💥 Join or support Team Mama Outspoken because hope is here—and together, we can help a mama find it. 💛  

We hope you'll join us next time! —Jill & Bobby  

You are invited to find community with us—check out the Mama Outspoken Village here. To learn more or grab your copy of the book, head here. Remember, you’re not alone in this. One of our favorite resources is the Postpartum Resource Center of New York—you deserve support that sees you.

Mark as Played

Advertise With Us

Popular Podcasts

Stuff You Should Know
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

On Purpose with Jay Shetty

On Purpose with Jay Shetty

I’m Jay Shetty host of On Purpose the worlds #1 Mental Health podcast and I’m so grateful you found us. I started this podcast 5 years ago to invite you into conversations and workshops that are designed to help make you happier, healthier and more healed. I believe that when you (yes you) feel seen, heard and understood you’re able to deal with relationship struggles, work challenges and life’s ups and downs with more ease and grace. I interview experts, celebrities, thought leaders and athletes so that we can grow our mindset, build better habits and uncover a side of them we’ve never seen before. New episodes every Monday and Friday. Your support means the world to me and I don’t take it for granted — click the follow button and leave a review to help us spread the love with On Purpose. I can’t wait for you to listen to your first or 500th episode!

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.