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Dating in the Second Half of Life

Debbie Weiss tells us about her journey after a tragic loss.

Listen to it here or on your favorite podcast platform:

In a heart-to-heart chat, our host Marianne Bailey and her guest, the ever-inspiring Debbie Weiss, author of “Available As Is: A Midlife Widow’s Search for Love” take us on a journey through the world of dating after 50, all from a woman’s viewpoint. They open up about the rollercoaster of emotions and experiences that come with stepping back into the dating game, especially after a significant loss. For Debbie, this new chapter began after the devastating loss of her dear George to cancer.

They go on to share that Grief isn’t always tied to the loss of a loved one through death. Sometimes, it’s the end of a relationship, like a divorce, that can leave a deep emotional scar. The aftermath of such life-changing events can be just as heart-wrenching, and the thought of dating again can seem like a mountain to climb.

Navigating the maze of dating apps is another topic they delve into. They laugh about the challenges of trying to decode the true meaning behind people’s words on these platforms. The world of online dating can often feel like trying to solve a puzzle with missing pieces, making the quest for a compatible partner all the more adventurous.

Wrapping up their enlightening conversation, they discuss alternatives to the traditional dating apps. They highlight platforms like, where you can dive into activities you love while also meeting people who share your interests. They cheerfully remind us of the importance of staying active and following our passions, as it could lead us to stumble upon a partner who truly understands and appreciates us.

Debbie’s book “Available As Is: A Midlife Widow’s Search for Love” can be found here:

Marianne Bailey The HIP Senior Founder

Marianne Bailey is the passionate owner and founder of, a dynamic online platform dedicated to empowering, engaging, and connecting seniors with resources and information to help them live their best lives. As a natural extension of her commitment to supporting the senior community, Marianne is also the energetic host of The HIP Senior Podcast, where she sparks insightful conversations with fascinating guests from various fields, sharing their wisdom and experiences with her listeners.

Marianne's dedication to redefining the senior experience has garnered her a loyal following and made her a respected voice in the senior community. She continues to champion the idea that age is just a number, and that life after retirement can be filled with adventure, new challenges, and endless opportunities for personal growth.

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