Dating Over 50: What If It Doesn't Work Out?

In this episode, Dr. Lisa and Tony explore the mindset shifts necessary for embracing new relationships in midlife.

They talk about shifting from "What if it doesn't work out"? to "What if it does." They discuss overcoming fears, redefining success, and the importance of growth and flexibility in dating again. Chapters 00:00 Introduction: Embracing New Beginnings in Midlife 02:07 The Impact of Pessimism on Dating 04:04 Crawling Before Walking: Relearning How to Date 05:55 Changing Priorities and Self-Discovery in Midlife 07:49 The Role of Familiarity and Unfamiliarity in Choices 10:06 Expanding Horizons: Seeking New Options 12:02 The Power of Flexibility and Adjustments in Relationships 13:58 Growth Through Experiences and Saying Yes Again 16:09 Overcoming Fear of Failure and Success 18:06 Building Friendship as a Foundation 19:56 The Deepest Fear: What If It Works? 22:13 Living Fully and Embracing Change 24:11 The Importance of Being Open to the Unfamiliar 26:09 Learning from Every Experience 28:03 Shifting the Question: From What If to Who Might I Become 29:55 The Power of Growth and Saying Yes Again 31:47 Challenge: Saying Yes to Life and Love 34:11 Conclusion: Embrace the Journey of Self-Discovery Get our free Saying Yes Again Starter Kit .

D iscover why dating feels so exhausting after heartbreak—and begin rebuilding the one thing healthy love depends on: Trusting yourself again. Watch our episodes on YouTube Subscribe to our Apple podcast Subscribe to our Spotify podcast Follow us on Facebook SayingYesAgain TikTok