Finding Love Again After Loss
10/15/24 • 62 min
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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
Instagram | Website
Send a message direct to Emily
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
Leave a rating/review for this podcast with one click
Guest: Michael Bolton and Jennifer Osler-Bolton
Instagram | Website
Previous Episode
About the You Are More podcast with Emily Cave Boit
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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.
Next Episode
Learning to Blink – Victoria Arlen’s Story
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How do you go from a vegetative state to becoming a gold medalist, ESPN host, and Dancing with the Stars contestant?
Victoria Arlen shares her unbelievable journey of survival and resilience with Emily. Diagnosed with two rare neurological conditions at 11, Victoria was locked inside her own body for four years, unable to move or communicate.
But through faith, family support, and sheer determination, she fought her way back to life, learning to blink, speak, and eventually walk. This powerful conversation explores overcoming trauma, the importance of celebrating small victories, and living with purpose.
Victoria’s story isn’t just about recovery—it’s about embracing life’s hardships, finding joy, and inspiring others to do the same.
Listen For:
04:59 Learning to blink: A small action that started a massive comeback
11:57 Launching Project Walk Boston: A family’s mission to provide hope
23:36 Learning forgiveness after medical mistakes
55:33 Dancing with the Stars: Sitting in her old wheelchair for a special performance
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Guest: Victoria Arlen
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Contact Emily
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You Are More, With Emily Cave Boit - Finding Love Again After Loss
Transcript
Emily Cave (00:00:02):
When I was thinking about recording this episode today, it reminded me of a line that I wrote in my book, and I said, I kind of didn't know what I wanted to say, and I can't believe that this is my first episode, or that this is the first line in my book. And when I
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