We didn't leave
our values.
We just outgrew the map.
Founded by Chris and Esther — two people of deep faith who figured some things out the hard way, and built a place so you don't have to.
As two people who are both around the mid-century mark in age and both living our faith as best we know how, both navigating the same invisible wall — and both done pretending it isn't there.
"Unchaperoned doesn't mean lost. It means free."
How This Started
The honest version — because that's the only version worth telling.
The Templates Don't Fit Anymore
The dating advice you were given was written for people starting families. It assumed a first marriage. It assumed you were in your twenties, figuring out who you were. Nobody wrote a template for being in your forties or fifties, with deep faith, adult children, a full life already lived — and a heart that still wants real connection. Nobody wrote a template for being unchaperoned.
Three Real Problems
Dating non-members meant constantly explaining why faith wasn't just a habit but a foundation. Dating members in high-LDS communities sometimes meant navigating a culture of performance — projecting the polished, put-together version rather than the real one. And then there was a quieter gap: the church, which we genuinely love, has rich programs for singles — but those programs were built for a different life stage.
A Chance Meeting in Southern California
By one of those small miracles that only makes sense in hindsight, Chris and Esther both ended up in Southern California at the same time — visiting their adult sons — and matched on a dating app. Within twenty minutes, they realized they had been living parallel lives.
You Are Not Alone in This
They kept meeting people who hadn't figured that out yet. Her girlfriends. The women Chris had dated. The men Esther had dated. People who were struggling through dating apps with no framework, no community, and no one who understood. That gap — that unmet, deeply human need — is where Unchaperoned Life was born.
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Why "Unchaperoned"?
When we were young, someone was always guiding the path. Parents. Church leaders. The structure of school, then marriage, then family. There was always a next step, a clear lane, a chaperone.
Then, somewhere in our forties, all of that fell away. And for a moment — honestly — it was terrifying.
But then something else happened. We realized we had all this wisdom. More self-knowledge than we had at twenty-five. More financial stability than we had at thirty. More clarity about what we actually wanted from a relationship — and what we would no longer settle for.
Unchaperoned doesn't mean lost. It means free.
It means you get to write this chapter yourself. And that, it turns out, is the best part.
Meet Chris & Esther
Chris
Co-Founder · Engineer · Adventurer
Chris is in his early 50s. He graduated from MIT as an engineer and spent years as a management consultant traveling the world — running complex projects for large corporations, solving problems that required both analytical rigor and human understanding.
Outside of work, he has completed Ironman triathlons, swum the Catalina Channel, hiked through some of the most remote terrain in the American West, and is now deep into road racing.
What he was not prepared for was how hard it would be to find genuine connection as a midlife single man of faith. What actually worked was something simpler and harder: honesty, self-awareness, and the willingness to stop trying to optimize his way into a relationship.
Chris loves the faith and lives by its principles. He is the father of four, and brings both the analytical mind and the hard-won emotional wisdom to everything Unchaperoned Life does.
Esther
Co-Founder · CEO · Bee Princess
Esther is in her late 40s. Born and raised in Texas, she spent her college and early married years in Arizona before returning to Texas to run her family's beekeeping and bee removal business — a company she has been part of since childhood, when she was literally crowned a Bee Princess.
She has spent years helping organize and chaperoning midlife LDS cruises and group vacations. She knows this world from the inside. She has seen what people are really looking for when they sign up for those trips.
Esther is quick to laugh, almost always smiling, and constitutionally incapable of judging anyone. She is a temple-going Latter-day Saint and a mother of four.
And yes — the woman who used to chaperone midlife Mormon singles is now helping them live unchaperoned. We see the irony. We love it.
"She built a business from the ground up. She knows what it takes to do hard things with grace."
What We Believe
The principles that guide everything we do.
We believe you can honor where you came from without being held back by it.
We believe healing and humor belong together.
We believe real connection starts with being honest about who you actually are.
We believe living authentically and living faithfully are not opposites.
We believe the second half of your life can be the best half.
We believe you deserve a community that truly gets it — not just sympathy, but understanding.
Who This Is For
This is for you if...
- →You're a midlife single (40s–60s) from a faith background
- →You're quietly rebuilding after divorce or a major life transition
- →You feel like you don't quite fit at church as a single adult
- →You're hungry for real connection and practical skills
- →You want to understand yourself better before diving back in
- →You believe in doing the inner work, not just the surface stuff
This may not be for you if...
- →You're looking for casual hookup advice
- →You're openly hostile toward people of faith
- →You want a quick fix without doing any inner work
- →You're not ready to be honest with yourself yet
And that's okay. We're not for everyone — and that's by design.
You Are Not Alone in This
If you have ever sat in sacrament meeting feeling invisible because you are the only single adult in a row of families — we see you.
If you have ever tried to explain to a date why your faith matters to you and watched their eyes glaze over — we get it.
If you have ever felt the pressure to perform a perfect version of faith when the reality is a lot more complicated and a lot more human — we know that feeling too.
If you have ever wondered whether real, deep, values-aligned connection is still possible at this age — we are here to tell you it absolutely is.
This is not a place where you have to keep up appearances.
Welcome to Unchaperoned Life.