Connected Hearts: A Community for Midlife Women Ready for Something More Real.
Genuine connection, fresh perspective, and a place where you can be yourself, feel seen, and truly belong.
What is Connected Hearts?
Connected Hearts is a community for women in their 50s to mid 60s who want more than surface-level socializing.
At the heart are our guided gatherings – experiences that bring us together in a way that feels easy, engaging, and enjoyable.
Everything is thoughtfully structured so no one has to wonder what to say, or how to join in. You simply show up – and step into something that feels welcoming, safe, and inclusive.
No politics. No religion. Phones away.
Just presence – and space to be yourself.
We believe midlife isn’t a season of decline – it’s a time of possibility.
A chance to stretch beyond old patterns, try new things, and create a life that feels good on the inside – not just one that looks good from the outside.
We believe that becoming a better friend to ourselves is foundational to happiness, and each month, we explore simple, relatable ways to live that truth.
This is a community where women encourage and celebrate one another.
And because the connection doesn’t end when a gathering does, Connected Hearts becomes something you’re truly part of – not just something you attend. Through continued touchpoints and opportunities for ongoing connection throughout the month, relationships have space to deepen naturally over time.
Together, we’re shaping a midlife (and beyond) that feels expansive, vibrant, and fully our own – through a shared journey of growth, connection, and friendship.
Why I Created Connected Hearts
Most women I talk to say the same thing – they have people in their life, but not really anyone they feel truly close to. They’re busy, their kids are older or grown, maybe they’ve moved, maybe their friendships just kind of drifted. And they want something more but they don’t know how to find it, especially in midlife.
That’s how I felt, too. What I wanted was a circle of real women having real conversations – and real laughs – about relationships, identity shifts, growth, and everything that comes with this chapter, while showing up for each other, month after month.
When I couldn’t find anything like that (and I looked), I decided to create it.
What Happens at a Gathering
Our gatherings are the heartbeat of Connected Hearts. While each month has its own theme, every evening follows a thoughtful flow designed to help you relax, connect, and fully enjoy the experience.
Our consistent flow is the canvas; the changing monthly themes are the art. You always leave with something valuable – a new outlook, a practical takeaway, or simply feeling more like yourself again.
Common Questions
Free casual social groups are built on good intentions, but without real commitment, attendance becomes inconsistent and the dynamic can drift – sometimes into the kind of drama you were hoping to leave behind. Connected Hearts is a curated, facilitated community where everyone has made a real commitment to be there. That shared investment changes everything – and it’s a big part of why the friendships that form here feel so different.
There’s also nothing to organize, host, or coordinate. We handle everything – the structure, the facilitation, the experience itself. You simply show up and enjoy the evening.
And what happens in that evening goes well beyond socializing. Each gathering is thoughtfully guided by Cheryl, whose background in psychology and coaching creates experiences where real conversation unfolds naturally, fresh perspective emerges, and you leave feeling genuinely inspired – not just like you spent “a nice night out.” That combination of connection, substance, and joy is something a casual social group simply isn’t designed to deliver.
Connected Hearts is designed to create deeper connection – and that’s difficult to create in a constantly changing drop-in environment. When the same women gather consistently over time, conversations go deeper, it feels easier to be yourself, and relationships have space to naturally grow. Membership allows each gathering to build on the last – creating a stronger sense of familiarity, comfort, and community.
At the same time, we understand that some women prefer a little more flexibility as they get to know the community, which is why we also offer limited flexible participation options for women who aren’t quite ready for full membership.
Because what happens here goes far beyond a casual night out. Connected Hearts is a thoughtfully guided experience designed to foster genuine connection, personal growth, and shared joy – all within a warm, welcoming community.
Real connection doesn’t happen by accident. Every experience is intentionally designed and personally facilitated by Certified Life Coach Cheryl Dillon to create an environment where women feel comfortable showing up authentically and engaging more meaningfully.
The membership structure also serves an important purpose: it creates continuity, familiarity and shared investment within the group. As women continue gathering together, trust deepens, conversations become richer, and real friendships form.
Connected Hearts is about investing in yourself, your well-being, and the kind of support and belonging that become possible when women continue showing up for one another over time.
I totally get why it might sound that way. But think about it – you pay for a gym because showing up consistently is hard without structure and accountability, and because the equipment and instruction make your effort actually work. This is the same idea. You’re not paying to make friends. You’re investing in something most of us struggle to prioritize for ourselves.
Many people happily invest in therapy, coaching, retreats, yoga memberships, and wellness communities because those experiences provide intentional structure, expert guidance, and transformation. Connected Hearts was created with a similar philosophy in mind.
Every gathering is intentionally designed and personally facilitated by a Certified Life Coach (me) – centered around meaningful conversation, personal growth, genuine connection, and belonging. Each gathering helps women reflect, gain fresh perspective, connect more authentically, and walk away feeling lighter, inspired, and more like themselves.
The friendships that form here aren’t forced or transactional – they grow naturally through shared experiences, consistency, vulnerability, laughter, and mutual support. Real friendships don’t grow from a one-time event. They grow from showing up together, over time.
And honestly, the women who’ve joined tell me it’s some of the best money they spend.
The gathering is once a month on the same evening, so most women find it’s actually easier to protect than something that moves around. You put it on the calendar and it’s just part of your month.
That said, life happens. If you occasionally can’t make it, you won’t lose your place in the community – the mid-month Connection Call and Unplugged social meetups keep you connected between gatherings. And because the same women come back every month, you can pick right up where you left off.
What we ask is that you show up with intention most of the time – because your presence matters to the women in the room, and theirs matters to you. That consistency is what makes this community feel different from everything else you’ve tried.
Our members are generally in their fifties to mid-sixties, though what matters most is where you are in life rather than the number of trips around the sun you’ve had. The conversations and themes reflect the experiences of women in this particular season – rediscovering themselves, reimagining what’s next, and building the kind of friendships that make this chapter feel full. If that resonates with you, you’re likely in the right place.
Many women attend their first gathering without knowing anyone in the room. That’s why Connected Hearts gatherings are intentionally facilitated rather than left to chance.
Through thoughtfully designed activities and guided conversations, the evening unfolds in a way that naturally helps everyone feel included and comfortable participating at their own pace. You’re never put on the spot, and there’s no pressure to share more than you’re comfortable with.
Most women tell us the same thing afterward: they arrived a little unsure… and immediately felt at ease.
To maintain our focus on genuine connection and personal well-being, Connected Hearts may not be the right fit if you’re looking for:
- Business Networking: While we celebrate each other’s successes, our primary goal is heart-centered connection. If your main objective is to pitch a product or build a lead list, this isn’t the space for you.
- Surface-Level Only: Connected Hearts is designed for those who want to move past small talk. It may not be a fit if you aren’t comfortable exploring fresh perspectives or engaging in conversations with a bit more depth.
- Divisive Topics: To ensure our space remains a sanctuary of peace and positivity, we do not discuss politics or other polarizing subjects. We are here to focus on what connects us, not what divides us.
