Dating in midlife can feel strangely hard, even when you’ve done the work, built a full life, and know yourself better than ever. If you’ve ever thought, “Why is this still so complicated?” this episode is for you.
In this conversation, I sit down with Rachel Greenwald, Harvard MBA and veteran matchmaker who has helped guide nearly 1,000 marriages. With warmth, humor, and deep insight, Rachel reframes dating not as luck but as a learnable skill, especially in midlife.
Together, we explore:
- Why the people who make us happiest don’t always match our dating checklists
- How chemistry can fool us and what actually leads to lasting connection
- The quiet dating rules that keep smart people single
- Why love often shows up in unexpected packages
- How modern couples are redefining partnership, including living apart together
This is a hopeful, practical conversation about dating with wisdom, curiosity, and openness, not fear or frustration.
👉 Listen or watch now and discover why midlife may be your most meaningful, and romantic, chapter yet.
Timestamps:
00:46 Meet matchmaker Rachel Greenwald
03:36 From Harvard MBA to professional matchmaker
04:03 A midlife pivot that changed everything
07:29 The highs and lows of matchmaking
09:44 What is keeping people single
10:20 The most powerful question in dating
13:11 Chemistry vs compatibility & happiness
17:11 Why we repeat unfinished relationship patterns
19:46 Why dating checklists can backfire
22:39 Why men make up most matchmaking clients
25:08 Why parents hire matchmakers for young adults
28:03 Why midlife dating isn’t hopeless
35:57 The three must-haves that really matter
38:26 Living apart together and modern relationships
44:51 Inside the Santa Fe dating workshop
48:27 Wisdom bumper sticker
53:11 Final takeaways on love and dating in midlife
Learn more about MEA at https://www.meawisdom.com/
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