If you’ve ever wondered, “Is it too late for me to...” the answer’s NO and The Uplifters are about to show you why. This space is for purpose-driven women who want to do big, brave things in the second half of their lives. I’m your host, Aransas Savas, and I’ve spent the last 20 years at the intersection of behavior change research and coaching.
This month, our theme is LOVE. We’re exploring:
💓 Mother love with Ruthie Ackerman (author of The Mother Code) on understanding the women who raised us, reconciling feminism and mothering, and reimagining this path in a way that feels right and true for ourselves. Listen HERE
💓 Friend love with Patina with Dina Aronson + Dina Alvarez on how later-life friendships and collaborations can unexpectedly change our creative paths. Listen HERE
💓 Self-love with Wendy Harrop, who said a giant yes to herself even though it meant courageously ending her marriage, moving across the country, and upending all the personal and professional structures she built in the first half of her life. Listen HERE
💓 Human love in the age of AI with Susan Ruth, host of the Hey Human podcast Listen HERE
💓 Romantic love with Alyssa Dineen, a midlife dating coach who helps us rethink the stories we’re telling ourselves about navigating the mysterious and messy world of modern dating
TLDR: Rom-coms are propaganda. All that “eyes across the room, instant fireworks, I knew from the first second” stuff? It’s not just unrealistic — for a lot of midlife women reentering the dating world after divorce, loss, or a long stretch of putting themselves last, it’s actively getting in the way.
Alyssa Dineen has been through it — the slow unraveling of an 18-year marriage, the terrifying and exhilarating freedom of starting over in her early forties, the fumbling through apps and first dates and all of it — and she came out the other side not just with a partner she adores, but with career built around helping other women do the same.
She is warm and wise and refreshingly practical, and she has helped women find love at every age — including a woman who met the love of her life and got married at 84. So if you’ve ever thought “it’s too late for me,” listen to this episode.
Alyssa left her marriage in her early forties. The relationship had been deteriorating slowly (“oppressive” is the word she uses) and she stayed longer than she wishes she had. But when she finally moved out on her own, she felt free. And also completely untethered from herself.
“I really adapted myself to what he wanted me to be,” she told me. “Which in hindsight sounds so crazy, but I know a lot of people do that.” (More people than you’d think, honestly. We’ve talked about this on the show before — we really are the sum total of who we spend our time with, and that can work for us or very much against us.) Newly single with two young daughters and no roadmap, Alyssa decided to date because she just wanted to meet people, have fun, and discover who she was again.
With each new person she met, she was asked to describe herself, to tell her story, to decide what she wanted and what she wasn’t willing to give up anymore. “I was telling my story and realizing I had so much more to offer than I was led to believe during my marriage,” she said. She fell back in love with herself.
After two-plus years on the apps (Tinder, Bumble, all of them), she met Yoav on Tinder. The first date was fine. The second date was nice. The third date — she almost talked herself out of. But something made her say yes one more time. And on date four, everything clicked. They’ve been together almost nine years.
The Research
Brain science tells us that as midlife women our pattern recognition is exquisitely well-developed. When it comes to relationships, we know what a bad relationship feels like, even when it looked good from the outside. The challenge isn’t our judgment. It’s that our nervous systems are often still calibrated to an older version of “exciting,” one that mistakes anxiety for attraction and calm security for boredom. It’s not masochism. It’s a neural pathway that was built a long time ago that can be rewired.
The Four Date Minimum Rule
Alyssa has a rule she teaches all her clients: the four-date minimum.
“So many people are looking for that immediate connection — eyes meeting across the room, the chemistry, the spark, the fantasy,” she told me. “But that doesn’t exist in your 50’s. I’m sorry. It will develop — but it’s likely not going to happen in the first date or two.” She’s not talking about settling. She’s talking about recognizing that adults, who’ve been through hard things, take time to drop their guard. The real person doesn’t always show up until date three or four (and sometimes five or six).
Her test for whether to keep going? “Would I still want to be friends with this person?” If yes, you keep going. She’s watched the romance develop from there more times than she can count. One of her own coaches on her team went on five dates with a man she kept describing as “just so nice” before she finally admitted she really did enjoy being around him — and they got married last summer.
So many of us were trained to associate love with pain. With the mysterious guy who runs hot and cold. With butterflies that are more like nausea. “We’re all still looking for that feeling from when we were 16 or 17,” Alyssa said. But what that feeling actually is, is insecurity.
Lift Her Up
Find Alyssa at stylemyprofilenyc.com and follow her on Instagram at @stylemyprofilenyc and TikTok at @stylemyprofile. And if you know someone who’s navigating the dating world right now — send this episode their way.
If you loved this story...
This episode closes out our Love Series, which has been one of my favorites. Go back and spend time with the whole collection — we’ve explored mother love, self-love, and the deep magic of later-life friendship. And check out two of our top episodes about love in midlife, including Susannah Ludwig — an Academy Award-nominated film producer turned life transitions coach — who found deep love after divorce, and Lakshmi Rengarajan, a dating culture researcher and coach focused on midlife dating.
Can we talk about this episode?
What beliefs about love did you grow up with? I’d love to hear them in the comments. And if you’re in the dating world right now, or thinking about stepping back into it, share where you are.
