​​Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald
​​Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald  
Podcast: The Midlife Chrysalis
Published On: Fri Dec 19 2025
Description: 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 togetherThis 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 Greenwald03:36 From Harvard MBA to professional matchmaker04:03 A midlife pivot that changed everything07:29 The highs and lows of matchmaking09:44 What is keeping people single10:20 The most powerful question in dating13:11 Chemistry vs compatibility & happiness17:11 Why we repeat unfinished relationship patterns19:46 Why dating checklists can backfire22:39 Why men make up most matchmaking clients25:08 Why parents hire matchmakers for young adults28:03 Why midlife dating isn’t hopeless35:57 The three must-haves that really matter38:26 Living apart together and modern relationships44:51 Inside the Santa Fe dating workshop48:27 Wisdom bumper sticker53:11 Final takeaways on love and dating in midlife Learn more about MEA at ⁠https://www.meawisdom.com/#MidlifeDating #DatingAfter40 #DatingAfter50 #MidlifeRelationships #FindingLoveLaterInLife #DatingAdvice #ModernDating #RelationshipAdvice #DatingWisdom #MidlifeWomen #MidlifeMen #Matchmaking #LoveAfterDivorce #DatingOver40 #MidlifeChrysalis