
How to Date in Midlife with Confidence with Kerstin Rao
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About this listen
Assess how feeling career stuck is impacting you across ten areas of life - in 30 minutes. Then, decide what you want to do about it.
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Dating in midlife can feel like a minefield—swiping, bad dates, and wondering if you’ll ever meet the right person. But what if there was a better way?
In this episode, I sit down with Kerstin Rao, a midlife dating coach who went from disaster dates to finding her perfect partner by building a dating system that actually works. She shares her most outrageous dating fails (yes, there was a convicted felon), but more importantly, she explains how to date with confidence, clarity, and strategy—without wasting time on the wrong people.
✔ Why random dating leads to random results (and how to fix it)
✔ The biggest mistakes midlife daters make—and how to avoid them
✔ How to get crystal clear on what you actually want in a partner
✔ Why dating multiple people at once can help you make better decisions
✔ How treating dating like a career search can get you better results
Midlife dating doesn’t have to be exhausting—with the right mindset and system, it can actually be fun.