Search a title or topic

Over 20 million podcasts, powered by 

Player FM logo
Artwork

Content provided by Emily Cave, Stories and Strategies and Emily Cave. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Emily Cave, Stories and Strategies and Emily Cave or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.
Player FM - Podcast App
Go offline with the Player FM app!

Finding Love Again After Loss

1:02:30
 
Share
 

Manage episode 445263218 series 3601719
Content provided by Emily Cave, Stories and Strategies and Emily Cave. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Emily Cave, Stories and Strategies and Emily Cave or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.

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

Contact Emily:
Instagram | Website

  continue reading

Chapters

1. Finding Love Again After Loss (00:00:00)

2. The reality of love after loss (00:05:48)

3. Family concerns about dating a widow (00:17:22)

4. “Two separate husbands, not a competition” (00:34:29)

5. The reality of dating a widow: Compassion and patience (00:46:09)

16 episodes

Artwork
iconShare
 
Manage episode 445263218 series 3601719
Content provided by Emily Cave, Stories and Strategies and Emily Cave. All podcast content including episodes, graphics, and podcast descriptions are uploaded and provided directly by Emily Cave, Stories and Strategies and Emily Cave or their podcast platform partner. If you believe someone is using your copyrighted work without your permission, you can follow the process outlined here https://staging.podcastplayer.com/legal.

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

Contact Emily:
Instagram | Website

  continue reading

Chapters

1. Finding Love Again After Loss (00:00:00)

2. The reality of love after loss (00:05:48)

3. Family concerns about dating a widow (00:17:22)

4. “Two separate husbands, not a competition” (00:34:29)

5. The reality of dating a widow: Compassion and patience (00:46:09)

16 episodes

All episodes

×
 
Loading …

Welcome to Player FM!

Player FM is scanning the web for high-quality podcasts for you to enjoy right now. It's the best podcast app and works on Android, iPhone, and the web. Signup to sync subscriptions across devices.

 

Copyright 2025 | Privacy Policy | Terms of Service | | Copyright
Listen to this show while you explore
Play