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/

#MidlifeDating #DatingAfter40 #DatingAfter50 #MidlifeRelationships #FindingLoveLaterInLife #DatingAdvice #ModernDating #RelationshipAdvice #DatingWisdom #MidlifeWomen #MidlifeMen #Matchmaking #LoveAfterDivorce #DatingOver40 #MidlifeChrysalis

Feeling stuck in midlife? You might be in your chrysalis, not a crisis.

In this Wisdom Wednesday episode, Chip Conley breaks down why midlife often feels confusing and heavy, and why that “messy middle” is actually the beginning of real transformation.

Chip shares:

• The three stages of every transition and where most people get stuck

• What really happens inside the messy middle

• Why men and women experience midlife so differently

• How transitional intelligence (TQ) helps you move forward with clarity

If you’re wondering whether something is wrong, or whether you’re simply evolving, this episode offers the reassurance and perspective you need.

If you enjoyed this, follow the show, leave a rating, and join us next week for more Wisdom Wednesday insights.

Timestamps:

00:00 Film Festival & Holiday Mood

01:55 Crisis vs Chrysalis and the Hollywood Myth

05:15 The Three Stages of Transition

07:07 Emotions in the Messy Middle

09:33 Finding Your Through Line

11:21 Ritualizing Endings

13:16 How Men Experience Midlife

15:40 How Women Experience Midlife

15:53 Why Women Navigate Midlife Differently

19:27 Identity, Purpose, and Feeling Stuck

21:35 Chip’s Personal Midlife Story

22:42 Why Men Resist This Work

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeChrysalis #MidlifeTransition #MidlifeCrisis #MessyMiddle #PersonalGrowthJourney #LifeTransitions #ChipConley #TransitionalIntelligence #MidlifeWisdom #SelfDiscovery #MidlifeWomen #MidlifeMen #EmotionalWellbeing #LifeReinvention #GrowthMindset

What if midlife became your chance to ROAR, not retire?

In this powerful conversation, bestselling author and longevity visionary Michael Clinton shares why your 40s, 50s, and beyond are actually the most exciting and opportunity-filled decades of your life. From his rise to the top of Hearst Magazines to running marathons on seven continents and earning a new degree at 67, Michael reveals how reinvention is not only possible, it’s essential.

He breaks down the ROAR framework for reimagining your future, explains why “life layering” is the antidote to midlife crisis, and dives into the emerging world of longevity science, age-positive culture, and purpose-driven living. If you’ve ever wondered what’s next, or what’s possible, this episode shows you how to build a richer, more meaningful second half of life.

Watch now and start reimagining what your future can be.

Timestamps:

00:00 Michael’s Santa Fe moment

01:31 Early life, father’s influence, love of words

05:27 A career in publishing

08:02 Midlife awakening at 39

10:50 Climbing Kilimanjaro and building an adventurous life

12:32 Returning to school at 67

15:56 The ROAR framework begins

20:00 Ageism, language shifts, modern role models

25:13 Life layering and building new identities

27:45 Preparing for post-career life

29:01 Reinvention stories and reimagineers

30:51 Relationships, editing your circle, and support systems

35:25 Growth mindset and lifelong curiosity

37:33 Longevity insights and the next book

39:18 Why longevity is having a cultural moment

44:01 Why the US is falling behind on lifespan

45:22 Rethinking work, age diversity, and longer careers

49:56 Longevity clinics and new health models

52:57 Longevity travel and residential communities

54:35 Wisdom bumper sticker

Learn more about MEA at ⁠https://www.meawisdom.com/

#MidlifeReinvention #Longevity #PurposeAfter50 #ReimaginingAging #LifeLayering #ROARMethod #SecondHalfOfLife #HealthyAging #MidlifeAwakening #RewireNotRetire #AgingWell #LiveLongerBetter #MidlifeTransformation #ModernAging #LifelongLearning