The Midlife Chrysalis Why Dating Feels Hard in Midlife (Even for Smart People) | Rachel Greenwald
Dec 19, 2025
Rachel Greenwald, a veteran matchmaker and Harvard MBA, shares her insights into the challenges of midlife dating. She highlights why traditional dating checklists often backfire and reveals the most powerful question to ask when seeking a partner. Rachel emphasizes the difference between fleeting chemistry and lasting compatibility, urging listeners to embrace unexpected connections. She also discusses modern relationship dynamics, including living apart together, and the importance of broadening dating criteria in this chapter of life.
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Midlife Pivot From MBA To Matchmaker
- Rachel pivoted at 37 from corporate roles to writing a book about dating for flexibility.
- That book led her to 'fake it till I made it' into a 24-year matchmaking career.
Matchmaking Is Pattern Recognition
- Matchmaking relies heavily on pattern recognition and wisdom built over time.
- Rachel calls dating in midlife like shopping at TJ Maxx: you must dig, but gems exist.
Start With Who Makes You Happiest
- Ask who in your life makes you happiest to reveal core relationship needs.
- Use that answer to compare against your stated checklist and close the gap keeping you single.