Over 50. Single.
And done doing this the hard way.
You've tried the apps. You've gone on the dates that went nowhere. You've swiped until the hope ran out.
What if meeting someone felt more like running into them at a dinner party than sorting through a database?
That’s what throwback dating is…
A curated community for singles in their 50s and 60s who are living fully in this chapter of life — and ready to meet people who are doing the same.
who thrives here:
Throwback Daters are a specific kind of person. Active. Curious. Open. They show up to life… and they show up for other people.
This community is the right fit if you:
Lead an active lifestyle and take your health seriously
Are financially independent and invest in experiences, not just things
Are in a chapter of life where you have meaningful time and energy to invest in connection — whether that's an empty nest, a flexible lifestyle, or simply a decision that love is a priority right now
Are genuinely open… open-minded, open-hearted, and open to growth
Take pride in how you show up, in every sense of the word
Value real conversation over small talk
Are seeking a heterosexual relationship and ready to actually pursue it
This is an intentionally curated community. Applications are reviewed, and not everyone is accepted… not because anyone isn't worthy of love, but because the right fit matters for everyone.
This probably isn’t the right fit if:
You're just curious but not really ready to put yourself out there
You're not in a place where you're actively investing in your health and wellbeing
You're not ready to actively engage… whether that's showing up to events, connecting with members online, or doing the inner work that real dating requires
You're looking for something casual with no real intention behind it
We want this community to work for you, and that means being honest about fit upfront.
Applications are reviewed personally by Megan within 24 hours. If it's a great fit, she'll reach out via text to set up a quick 10-minute call. That's it.
Hear it from our happy couples:
Justin’s Story:
After spending a significant amount of time navigating online dating, I often found myself feeling uncertain, confused, and frustrated… with far too much time wasted.
That’s when I decided to attend a Throwback Dating event at the Shedd Aquarium (August 2025).
Upon arriving I spent ten minutes having conversations with guests, and it didn’t take long for me to catch the eye of a particular woman who was truly alluring. I immediately sat next to her, and for the next half hour we had an incredible conversation… the kind of connection you simply can’t get through online messaging or even a phone call.
It was a truly organic, in-person meeting, just like the old days - where you can look someone in the eyes and really get a sense of who they are.
Thirty dates later (yes, 30!), I’m happy to say we’re having a blast together.
What a great way to cap off the year! Thank you Megan and Throwback Dating!
Eden’s Story:
To me, Megan Wessels is an angel. She has a true gift for connecting great, high-quality people.
I was skeptical at first, but after she interviewed me, she connected me with an incredible gentleman… someone with the very qualities I had been praying for. Through that connection, I found my second chance at love.
Megan brings a modern, intentional approach to organic dating, and I’m deeply grateful for the way she helped change my life.
Rob’s Story:
Throwback Dating truly changed the course of my life.
The Throwback community helped me find myself again. Through the experience, I was able to open up to possibilities I didn’t even know existed, and I found a connection with a very special person I never would have met any other way.
I’m incredibly grateful for this community and for the way it helped me step into a new chapter of my life.
Kate’s Story:
Rob and I met at the very first Throwback Dating event either of us attended in February 2025... a small, curated charity poker night hosted in someone’s home. From the very beginning, it felt different from dating apps. In one evening, I had real conversations and meaningful connections with more people than I ever did through months of swiping. I remember thinking, I may not have met my match tonight, but I’ve met some interesting people I could genuinely see myself being friends with.
I had been married for 20 years and took several years after my divorce before dating again. When I finally tried the apps, I stayed on them for about a year - open to meeting someone, but never feeling like the process truly reflected who I was. When I met Megan and heard her vision for Throwback Dating, it felt like a relief: a way to meet people as whole humans, not dating profiles.
When I first met Rob, I felt a curiosity that made me want to get to know him better. When we finally went out a month later, I felt a strong connection that felt worth exploring. At the time, he wasn’t even looking to date... he came to his first Throwback Dating event hoping to make new friends during a difficult chapter of life. Ultimately, we spent three to four months simply spending time together as friends before ever calling anything a “date.”
That lack of pressure created space for trust, comfort, and safety to grow. We both carried past pain and understandable hesitation, but I believe the key to our success has been how the relationship has unfolded slowly and organically. We have a ton of fun together, we laugh a lot, there is a strong mutual attraction and we bring real joy to each other’s lives, and that feels amazing. It feels like a gift.
Ursula’s Story:
I’m a 55-year-old, self-employed woman in Chicago who was looking for a serious connection, and I was thrilled to discover Throwback Dating, created by Megan.
Through the opportunities Megan creates, I met someone who is serious, handsome, fun, and a true gentleman. I was looking for a high-quality human being… someone empathetic, caring, generous, and fun… and Megan was able to connect me with exactly the right person.
Her thoughtfully hosted events bring together incredible people and create genuine, meaningful connections. I’m so grateful for this experience.
Your person is out there. And they might already be in this community. We'd love to learn more about you.
Applications are reviewed personally by Megan within 24 hours. If it's a great fit, she'll reach out via text to set up a quick 10-minute call. That's it.