Finding Love After 40 — And the Fourth Date Rule

Finding Love After 40 — And the Fourth Date Rule

From The Uplifters by Aransas Savas

March 5, 2026 · 45 min

About this episode

Alyssa Dineen shares her insights on finding love online after 40 and discusses her 'four-date minimum' rule.

Alyssa Dineen: Midlife Dating Coach — Finding Love Online After 40 What does it actually take to find love in midlife — especially when you're starting over after a long marriage, navigating menopause, and swiping on apps you never imagined you'd need? For women over 40 returning to dating, the modern landscape can feel like a foreign country. Dating coach and author Alyssa Dineen found herself there too, leaving an 18-year marriage in her early forties and figuring out online dating in real time. Now she helps midlife women navigate the apps with confidence, strategy, and a lot less heartbreak. In this episode, you'll learn what actually works — from building an authentic profile that attracts the right match to her signature "four-date minimum" rule that has helped countless women find love they nearly walked away from. Alyssa brings both personal experience and professional wisdom to what it means to date with intention during this second act. Alyssa's own midlife reinvention took her from a difficult marriage to a coaching practice she built from scratch, helping online daters feel more empowered as they navigate connection in the second half of life. Her transformation is…

People in this episode

Host: Aransas Savas

Guest: Alyssa Dineen

Topics covered

  • midlife dating
  • online dating
  • finding love
  • personal transformation
  • dating strategies

Keywords

  • midlife dating
  • dating coach
  • online dating
  • four-date rule
  • women over 40

More episodes of The Uplifters

Explore listener stats, chart rankings, contacts and more on the The Uplifters podcast page.