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 proof that it's never too late — including the 84-year-old client who met the love of her life and got married.

What You'll Learn:

How to find love online after 40 — Alyssa's proven strategy for online dating success in midlife, including which apps actually work for women over 40

Why the "four-date minimum" changes everything — what science and experience both tell us about chemistry, attraction, and why we give up too soon

Midlife reinvention through dating — how getting back out there after divorce can become a profound act of self-discovery for women over 40

Building confidence after 40 as a female founder — how Alyssa turned her own second-act experience into a thriving coaching business

How to create an authentic dating profile — why repelling the wrong matches is a strategy, not a failure, for women seeking meaningful connection

Starting over during midlife transition — what to do when modern dating technology feels completely overwhelming

Perimenopause and romantic connection — understanding how our nervous systems can mistake anxiety for attraction, and how to rewire toward healthier love

Key Timestamps:

0:00 - Introduction & Join the Tribe sponsor

1:30 - Welcome to the Love Series finale

2:00 - Statistics on dating after 50

3:00 - Introducing Alyssa Dineen

4:30 - Alyssa's 18-year marriage and the decision to leave

6:45 - Rediscovering herself through dating in her early forties

8:15 - Meeting her partner on Tinder and how Style My Profile was born

11:00 - The parallel between career reinvention and dating reinvention

12:45 - Authenticity in dating profiles and why we hide ourselves

16:30 - The four-date minimum explained

17:00 - Looking back at Alyssa's own four dates with her partner

21:00 - When to keep going vs. call it done

23:00 - The science of neural pathways and old relationship patterns

26:00 - Why we chase the wrong kind of "exciting"

30:15 - Navigating dating app technology in midlife

33:00 - Why you need a strategy (not just an app) to find love

36:00 - The most important thing midlife women should know about finding love

38:00 - Curiosity as the single most powerful dating tool

39:15 - Alyssa's new podcast: The Dating Lab

40:00 - Self-care and the radical practice of napping

42:00 - How to find and support Alyssa

Key Takeaways:

For midlife women returning to dating: The "four-date minimum" isn't about settling — it's about giving real connection time to develop past the walls we've built from years of lived experience

For women over 40 seeking purpose and love: Your dating journey can become a second-act reinvention story; the same curiosity and openness that helps you find love helps you find yourself

For perimenopause entrepreneurs and career changers: Alyssa's path from difficult marriage to thriving business owner is a masterclass in turning personal pain into professional purpose

For anyone who thinks it's too late: A client found love and got married at 84. The data on midlife online dating is actually quite good — 72% of singles aged 43-58 report their online dating efforts led to a real romantic relationship

Featured Quote:

"It is not too late. I hear this from women who are 40, 45, 50, 60 — everybody thinks they've waited too long. It is not too late." — Alyssa Dineen

Resources & Links:

Alyssa's website: stylemyprofilenyc.com

Instagram: @stylemyprofilenyc

Personal Instagram: @alyssadineen

TikTok: @stylemyprofile

Alyssa's podcast: The Dating Lab (available on all major platforms)

Join the Tribe: jointhetribe.com — use code UPLIFTER20 for 20% off your first order

About Alyssa Dineen:

Alyssa Dineen is a published author, dating coach, and founder of Style My Profile NYC — a transformative coaching practice helping online daters feel more confident and empowered as they navigate modern dating. After leaving an 18-year marriage in her early forties, Alyssa rebuilt her life and found love through the same process she now teaches. A true midlife reinvention story, Alyssa's work helps women over 40 approach dating with strategy, authenticity, and hope.

About Your Host:

Aransas Savas is a wellbeing and leadership coach specializing in helping women over 40 navigate midlife transitions, career changes, and second-act reinvention. With 20+ years of behavioral research experience partnering with companies like Disney, Weight Watchers, and Best Buy, she hosts The Uplifters Podcast, featuring women doing transformative work in the second half of their lives. Aransas brings both research rigor and personal experience to conversations about courage capital, midlife transformation, and building meaningful second acts.

Connect with Aransas:

Instagram: @aransas_savas

Podcast Instagram: @the_uplifters_podcast

TikTok: @theuplifterspodcast

Facebook: Aransas Savas

Website: theuplifterspodcast.com

YouTube: @theuplifterspodcast

LinkedIn: Aransas Savas

Keywords:

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