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How do you navigate love after loss?  

Emily sits down with Jennifer Osler-Bolton and her husband Michael Bolton, a couple that found love after Jen’s devastating loss of her firefighter husband, Ryan.

Their candid conversation explores the unique challenges of dating a widow, blending families, and how to honor a late spouse while embracing a new love.  

Through humor, wisdom, and raw vulnerability, they reveal the delicate balance of moving forward while cherishing the past, and how Michael’s love for Jen extends to protecting Ryan’s memory.  

This is a powerful exploration of grief, love, and resilience. 

Listen For:
5:48 – The reality of love after loss
17:22 – Family concerns about dating a widow
34:29 – “Two separate husbands, not a competition”
46:09 – The reality of dating a widow: Compassion and patience 

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Guest: Michael Bolton and Jennifer Osler-Bolton
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Send a message direct to Emily

Emily Cave Boit shares her journey of creating the website *You Are More*, which began nearly 10 years ago as a space for people to share their struggles and stories.

In 2020, after the sudden loss of her husband Colby Cave, she shut down the site while grieving during the pandemic. Now, four and a half years later, she’s relaunching the website and adding a podcast, with a renewed focus, emphasizing that people are more than the labels or traumas they face. Through open conversations about loss, trauma, hope, and triumphs, Emily and her guests aim to help others heal and feel seen.