When Hims & Hers co-founder Stephen Boynton started exploring improv performance a few years back, it was a bucket-list moment. “I took an improv class at Theatre 99 on a whim,” he says. “It had been something I wanted to try. It was one of those things like skydiving, the fear of being in front of an audience and not knowing what I was doing. There was sort of a thrill-seeking thing going on there.”

And after one class, Boynton was hooked. “I had so much fun with it I thought I could do it every night of the week,” he says. “It’s one of those things where when you start out, you fail a lot, but you have these moments where you’re successful onstage and they’re so powerful. That’s what you’re chasing for the rest of your life in improv. You’re just looking for that moment of pure connection. To have the audience laugh it’s something that you and the other person onstage can understand.”

That moment of connection led Boynton to form a trio with fellow imrov-ers Nate Rufo and Hunter Gardner for some three-on-three competitions, but Boynton says that the plan was always to expand the troupe. “You want a diversity of people with different backgrounds, so we wanted an even mix of men and women,” he says. “We wanted people who were like-minded in the way they want to approach improv.”

Now a team of eight, the group has come a long way since 2013. But Boynton says that moment of fear he first felt walking onstage with nothing planned is still with him, as it probably is with all improvisers. “You don’t ever really get all the way past the fear,” he says. “You just learn how to manage it, and you learn how to focus. When you start off, all there is is fear. You do a lot of knee-jerk reaction stuff that you think is funny, as opposed to just trying to be real. And what you do is you progress as you’re onstage enough times in front of enough people that you’re able to just focus on your partner and listen and make the scenes make sense. That’s when the magic happens.”

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