Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald
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:
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.
