Winter Garden Social
One group is proving you don’t need
a label—or a plus-one—to belong.
- Heather Lee
- Fred Lopez
When Matt Bergin’s marriage ended, it wasn’t just a divorce. It was a social freefall.
“For the first time in 20 years, I didn’t have any friends,” he says. “People choose sides in a divorce, and I was suddenly on the outside, starting over.”
At first, he joined a singles group, but that didn’t quite fit. It wasn’t about relationship status, it was just about connecting. He wanted a space where anyone could show up, be seen, and feel like they belonged.
So he built it.
In August 2024, Matt launched Winter Garden Social, a group where singles, couples, and “it’s complicateds” all belong. Think of it as therapy with a side of trivia night—no awkward icebreakers, just connection.
Trivia evenings, speakeasy outings, and pop‑up adventures have drawn a steady crowd of 40–50 regulars and nearly 1,400 online members. Some events are Matt‑led; others are member‑created.
“It’s meant to be a social network in real life,” he says. “You don’t have to come with anyone. You just show up—and friendships happen.”
The magic? It’s low‑pressure. Come once or come weekly. Stay quiet or dive in. “The hardest part of adulthood is finding new people to do life with,” Matt says. “This group gives you that—community, without strings.”
Divorce may have stripped Matt of his old circle, but Winter Garden Social gave him something bigger: a new family of friends. And if you’re looking for your people? They’re saving you a seat.
The hardest part of adulthood is finding new people to do life with. This group gives you that—community, without strings.
Want to join?
When: Events happen weekly and vary by theme—think happy hours, trivia, escape rooms, and more. Check the Facebook group for the latest schedule.
Where: All around the Winter Garden and Clermont area.
How It Works: Just show up! Most events are casual, come-as-you-are gatherings. Most are free, some may have a small fee (like a ticketed event), but all are focused on creating real, local connection.
Learn More: Join the Facebook group at or visit Instagram @wintergardensocial
