Today we’d like to introduce you to Melissa Hesse.
Hi Melissa , can you start by introducing yourself? We’d love to learn more about how you got to where you are today?
The Story Behind Eventurous Singles
After moving back from Germany, I found myself mourning an entire life I had built. I had rediscovered who I was there—great friends, strong community, and a life I truly loved.
Coming home, I was optimistic. I expected to rebuild that happiness. Instead, I was met with the stigma of being single, loneliness, and the exhausting reality of dating apps. Having my kids with me full time in Germany and then every other weekend after moving back, was one of the hardest adjustments. As I was trying to rebuild a life after divorce, Time to meet people was limited, and dating apps felt draining and discouraging.
People always say, “Go do what you love to meet your person.” So I did. I went hiking and kayaking, but I often found no one there. That’s when I realized: if the people weren’t where I was going, I needed to bring the people to me.
So I started a singles hiking and kayaking group.
Almost immediately, I found others going through the same experiences. We connected, formed friendships, and built a growing community where people were truly finding their people.
But as the group grew, it became overwhelming to manage as a free Facebook group. I was spending 10–12 hours a day moderating, handling conflicts, safety concerns, and increasingly complex situations. We weren’t running background checks, liability issues, and I even received threats of lawsuits. The community was too important to lose, but it needed structure.
After a lot of thought, I turned it into a business.
We implemented background checks, structured events, and created systems focused on safety, inclusion, and consistency. Most importantly, we built a place where people feel welcome.
What started as a small group has grown into something much bigger—a real community. People form friendships, support each other, celebrate milestones, and show up for one another in meaningful ways.
Many members have found their closest friends here, and some have even found their person. But most keep coming back because they remember what it felt like to walk in alone—and they want others to feel included too.
At its core, Eventurous Singles is about connection. It’s about creating a space where people feel seen, supported, and part of something bigger than themselves.
What started as a hiking and kayaking group has become a community built on kindness—and that’s what it will always be.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
The transition into the business was anything but smooth.
From the moment I announced I was turning the group into a business, everything changed. One day people were treating me like a hero. The next day, some people viewed me as the villain.
What many people didn’t see was the pit in my stomach that I carried for months. I wasn’t trying to take something away from anyone. I was trying to save it.
I was trying to keep the community alive while making it safer, more organized, and sustainable, while also protecting myself from the burnout that comes from carrying the weight of an entire community.
When you bring together hundreds of people, you also bring together hundreds of opinions. As the person making decisions, I quickly learned that every decision would make someone happy and someone else very unhappy.
The reality is that 99.9% of the community was supportive, grateful, and kind. But if you’re not careful, that tiny fraction of negativity can become louder than all the positivity combined.
As someone who has always been a people pleaser, one of the hardest lessons I had to learn was that I could not make everyone happy. Eventually, I stopped making decisions based on the loudest voices and started making decisions based on what was best for the community as a whole.
Most importantly, I learned to develop a thicker skin. Not because I stopped caring, but because I cared too much to quit.
Every time I considered walking away, I thought about the lives being changed, the friendships being formed, and the people who had finally found a place where they belonged.
Those people reminded me why I started. And they reminded me why it was worth continuing.
Alright, so let’s switch gears a bit and talk business. What should we know?
Eventurous Singles is more than a social group—it’s a community built around helping people get out of the house, reconnect with themselves, and start putting their own life first again.
We focus on more than meeting people. We focus on growth. That means trying new things, pushing yourself outside of your comfort zone, picking up hobbies again (or discovering new ones), and showing up for life instead of waiting for someone else to show up.
We offer over 30 events a month in which we create a safe, welcoming experiences for singles across Metro Detroit where people can walk in alone and immediately feel included. Many assume we’re a dating group, but our real purpose is helping people build friendships, support systems, and meaningful connections while they become the best version of themselves.
Our events are intentionally diverse so there is something for everyone—hiking, kayaking, golf outings, game nights, concerts, travel experiences, charity events, taco Tuesdays, sporting events, holiday parties, and large social gatherings. Every event is designed to attract like-minded people who are also choosing to show up for themselves.
What sets us apart is our people. We have the kindest most caring people. We don’t just post events—we plan them, host them, and build an environment where people feel safe, seen, and included from the moment they arrive.
What I’m most proud of is watching people transform. Members don’t just meet people—they regain confidence, build friendships, find their people, and start living again. Many tell us the same thing: they didn’t just find a group, they found a reason to get out, try harder things, and prioritize themselves again.
At its core, Eventurous Singles is about one thing: helping people step out of isolation and into a life that feels full again—one event, one connection, and one brave “yes” at a time.
Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
The credit for this group truly goes to everyone who shows up and continues to spread kindness and lift others up. This community would not exist without our incredible hosts, who give their time, energy, and hearts to help change people’s lives—they are the true heart of it all.
During the transition, I was especially supported by three amazing women—Crystal Shounia, Michelle Gabriel, and Melissa Filippis. Their belief in the vision, along with the dedication of so many hosts, made it possible to keep this community alive and thriving.
I am deeply grateful for all of them. If I didn’t have their support, and the continued support of every person who shows up as a “magnet of kindness,” this community simply would not exist. Every member plays a vital role in what this has become.
Special shoutout to Crystal Shounia, Executive Event Planner, for the endless work planning events, and to Amy Morris and Michael Randall for always stepping up to host and bring people together.
Most importantly, the continued support my kids give me, despite how busy I am with this group. They recognize how this is impacting the lives of many others.
Pricing:
- $20 a month
Contact Info:
- Website: https://www.EventurousSingkes.com
- Instagram: @Eventurous_Singles
- Facebook: https://www.facebook.com/share/g/1GwA6L4enx/?mibextid=wwXIfr
