In this powerful and deeply reflective episode, Alyssa Dineen sits down with iconic stylist, designer, author, and midlife advocate Stacy London for a conversation about identity, confidence, aging, and the evolving meaning of personal style.

Best known as the co-host of What Not to Wear, Stacy shares how her philosophy has shifted from prescribing fashion rules to helping people reconnect with their own agency and intuition. She opens up about the emotional impact of being judged publicly, the limitations of trend-driven fashion, and why clothes alone can never be the source of true confidence.

Alyssa and Stacy explore the intersection of style, self-worth, and midlife transition, including menopause, women’s health, and why this life stage deserves more honesty and visibility. They discuss sustainable fashion, vintage shopping, overconsumption, and how building a wardrobe with intention can reflect who you are now—not who you used to be.

This episode is an empowering reminder that style is not about fitting in or fixing yourself, but about trusting what makes you feel alive.

1. (01:00) Stacy’s evolution from What Not to Wear to personal empowerment
2. (03:10) Why modern culture no longer needs traditional style “experts”
3. (04:20) The difference between personal style and trends
4. (05:45) Constructive criticism, judgment, and agency in fashion
5. (07:00) The emotional impact of public scrutiny
6. (08:15) Stepping away from the mirror and redefining confidence
7. (10:00) Why clothes can’t be the foundation of self-esteem
8. (11:20) What’s broken in the fashion industry today
9. (12:45) Why women are underserved by fashion brands
10. (14:30) Midlife style challenges and finding the middle ground
11. (17:10) Why vintage shopping supports individuality
12. (18:30) Favorite vintage and resale platforms
13. (22:40) How to shop vintage with intention
14. (25:00) Clothing swaps, resale, and circular fashion
15. (27:00) Building a wardrobe with “character builder” pieces
16. (28:55) Overconsumption and fashion’s environmental impact
17. (31:30) Midlife transitions and living with more presence
18. (33:00) Why Stacy closed State of Menopause
19. (35:40) Menopause as a health and lifestyle issue
20. (37:30) The business of menopause and women’s health
21. (38:50) The emotional costs of...

In this insightful and grounded episode, Alyssa Dineen sits down with celebrity dating coach, media personality, and bestselling author Damona Hoffman to break down the biggest misconceptions in modern dating, and what actually leads to lasting connection.

Damona shares how dating apps changed the landscape of relationships, why over-texting creates false intimacy, and how chasing instant chemistry can distract us from true compatibility. Drawing from years of coaching experience and her own love story, she explains why dating works best when treated as a process rather than a spark-driven guessing game.

Alyssa and Damona also unpack outdated dating rules, shifting gender norms, and how communication breakdowns contribute to dating burnout. Together, they offer practical guidance for moving off the apps, setting realistic expectations, and building attraction over time, without losing yourself in the process.

This episode is a refreshing reality check for anyone feeling confused, discouraged, or overwhelmed by modern dating.

1. (01:00) Damona’s background and how she became a dating coach
2. (02:30) Translating personal branding principles into dating profiles
3. (04:40) Why dating apps became essential, and who they actually serve
4. (06:10) The communication crisis in modern dating
5. (08:30) Dating burnout and the illusion of connection through texting
6. (09:25) Why you can’t truly know someone through messages alone
7. (11:20) The “one-to-one rule” and when to move off the apps
8. (13:45) Phone calls vs. first dates as screening tools
9. (15:15) Managing expectations and emotional energy in early dating
10. (17:00) Letting go of outdated dating rules and gender roles
11. (19:30) How relationships and marriage have evolved
12. (20:30) Reciprocity over rigid roles in modern partnerships
13. (23:25) Damona’s real-life dating experiment, and how she met her husband
14. (27:00) Why dating should be treated as a process, not a vibe
15. (30:00) Rethinking distance, flexibility, and logistics in dating
16. (35:40) How dating needs change across different life stages
17. (38:15) Questioning inherited stories about love and romance
18. (39:05) Chemistry vs. compatibility, and why chemistry alone isn’t enough
19. (40:50) The three-date rule and how attraction actually builds
20. (44:15) Rom-com expectations vs. real-life...

In this fun, honest, and incredibly relatable episode, Alyssa Dineen sits down with dating coach and creator of Finding Mr. Height, Ali Jackson, for a conversation about burnout, rebuilding joy in dating, and the surprising way she met her current partner through real-life events—not apps.

Ali shares the story of how she unintentionally became a dating creator through her Close Friends list, the monotony of going on endless “okay but not great” dates, and the mindset shifts she used to keep going even when dating felt exhausting.

Alyssa and Ali dive into the realities of modern dating: messaging fatigue, over-attaching to outcomes, relying too heavily on apps, and what happens when you finally decide to start showing up in-person again. They get into the full story of how Ali met her partner—including the event that changed everything, the 4AM bar moment, the “Skyline” nickname, and why taking initiative ended up being such a good thing.

If you’re feeling drained by dating or unsure how to keep going, this episode is a reminder that connection can show up when—and where—you least expect it.

• (01:50) How Ali’s Close Friends list accidentally turned into a dating community
• (03:50) Sharing more publicly during the pandemic and finding her voice
• (05:00) Experiencing dating burnout from endless “meh” dates
• (10:20) How to find excitement in dating without attaching to outcomes
• (12:30) The simple post-date question that changes everything
• (15:30) Why texting too long creates false chemistry
• (19:30) The moment Ali realized she needed to date differently
• (20:20) Her commitment to attending two in-person events a month
• (21:20) Viewing events as opportunities—not pressure-filled missions
• (23:00) The April event that set everything in motion
• (31:30) Staying out until 4AM and how “Skyline” got his nickname
• (33:15) Why Ali decided to ask him out first
• (35:00) Why finding love later made the relationship stronger
• (37:05) Embracing your “weird” as the best dating filter

Listen on Apple Podcasts, Spotify, or anywhere you get your podcasts.

If you enjoyed this episode, please rate, review, and share—it helps others discover the show!

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