These days, Preston Thomas gets the question so often that he’s come up with a stock answer. How, friends and colleagues and relatives and pupils and barroom gawkers want to know, did he get so interested in picking locks?

Simple. “Misspent youth.”

On a recent Wednesday evening, Thomas, a telecommunications lawyer at Jones Day, is waiting for a crowd to amass on the second floor of the Board Room, a game-themed bar in Dupont. The landing is marked off with the rather unlawyerly sign “RESERVED FOR PRESTON THOMAS AND HIS SCOFFLAWS.”

Below, revelers are drinking Shiner Bock and rolling dice. Upstairs, the gathering quickly swells to about 50 people—hackers, hipsters, libertarians, some new, some repeat customers—who’ve come to participate in one of Thomas’ monthly gatherings. The lesson: how to pick locks.

Thomas, 30, is the president of the D.C. chapter of the Open Organisation of Lockpickers, or TOOOL, a “locksporting” group whose mission is to “advance the general public knowledge about locks and lockpicking,” and which advertises its free tutorials on sites like Meetup. TOOOL was founded in the Netherlands in 2002, and now has chapters in cities like Boston, New York, Cleveland, and Phoenix. The appeal is clear: “I feel like it’s pretty badass to know how to pick a lock,” says Macy Maddux, a first-timer, when I ask her why she came. Jake Johnson, who first heard of the classes on Reddit, says he’s hoping to gain a new skill. “I hope I can lock myself out of the house less.”

Once everyone’s settled in with a beer, Thomas introduces himself and hands the floor to the night’s instructor—a brawny Department of Defense employee named Robert Pingor. With his closely cropped hair and tattooed, beefy arms, Pingor’s the type of guy you’d expect to teach MMA, not hang out in a bar whose chief appeal is that it’ll let you bring your own pizza and play Connect Four. Lock picking, Pingor explains, is actually fairly simple. You just need two gadgets: a pick and turning tool. The turning tool goes into the bottom of a lock’s keyhole, and the pick fits into the space above. The trick is to apply gentle pressure to the turning tool while tripping tumblers in the lock, one at a time, with the pick.

Pingor demonstrates with one of his practice locks. A little turn here, a couple twists there, and it’s open. Then he and Thomas pass out practice locks and picks and put the crowd to work.

Pingor, a part-time consultant through a private security firm, spends much of his time outside the Pentagon breaking into businesses across the country. He enters by whatever means necessary: disguises, fake IDs, lock-picking. “The goal is to get to some high security target,” Pingor tells me later. Once he has his hands on a secured database or some other high-value target, he trains businesses how to prevent such an attack again.

As soon as he hands me my first test, a dinky little lock with just one tumbler, Pingor asks me to follow him to the upstairs bar, which is unmanned. Is he going to tell me a secret? “Come here, I want to show you something,” he says. I follow him. He steers me toward a nondescript closet with double doors, and unveils a hooked gadget, slips it over the lock between the doors, and pops the lock open. This is the bar’s liquor cabinet, filled with thousands of dollars’ worth of booze. “Security is only an illusion,” he tells me as he shuts and locks the door. Whoa.

By the time I sit down, many students have already conquered their second or third locks. I’m still busy on my first. It’s hard work. I close my eyes and visualize a microscopic version of myself working the tumblers from within the housing. I try to Zen my way into it, to feel the lock through the pick as an extension of my own body. No luck. Pingor sees me struggling and hands me another tool. It’s serrated, not hooked. “Rake this one back and forth,” he says. I do. The lock opens with sinful ease, and I’m one step closer to a life of crime.

“Ready for the next one?” Pingor says, reaching into his box of locks. Around me, some students have graduated from practice gadgets to padlocks, deadbolts, and handcuffs. Newcomers, who just 30 minutes ago couldn’t tell you how a lock works, are picking open heavy padlocks, the kind of thing you’d expect to keep safe a cache of illegal weapons or the Ark of the Covenant. I grab one, too, but achieve no glory. My life of crime ends before it begins.

Pingor, who leads the Maryland chapter of TOOOL, says he got into lockpicking because “I got bored of solving Rubik’s Cubes. I needed something to channel my energy into, and lockpicking seemed like an interesting skillset to have.” Thomas’s involvement began the way a lot of hobbies do, with a nagging interest. “I had been interested for a long time,” he says. In 2009, he bought a set of picks and started to experiment. “Part of the reason this is so fun is because it’s completely opposite of what I do day-to-day,” he says. By day, Thomas is a telecommunications lawyer, but by night, he’s Jason Bourne. And that felt good. As his skills improved, he ran across other enthusiasts, which led him to TOOOL, and ultimately, to founding its D.C. chapter.

Thomas knew he wanted to share his passion for picking with others, but he had to find a venue for meetings. He emailed Board Room’s owner, Beth Lindsay, with his idea. It was the first venue he approached. “I was a little leery at first,” Lindsay says. “I got this email saying…we’re gonna teach people how to pick locks.” But when Thomas elaborated on the idea, Lindsay relented and agreed to host a test meeting. The prospect of some extra beer sales probably didn’t hurt, either.

Still, Lindsay’s initial apprehension was understandable: Isn’t it irresponsible to teach a skill commonly associated with burgling? “The public perception is that the only application of lockpicking is unsavory,” Thomas says. “We’re trying to dispel that perception.” Each year, TOOOL D.C. hosts a lock-pick village at the ShmooCon, an annual hacker convention in D.C. There, Thomas organizes events like pick-and-swap competitions and something called “Gringo Warrior,” a game that takes place in a fictional Mexican prison in which players must circumvent handcuffs, a locked door, a guard, and sometimes a ninja in order to escape. All in all, it’s geeky fun, in the vein of something you’d find at a comic book convention.

Like tinkering with cars on the weekend or mastering a martial art after work, lockpicking does have some useful applications, but none you should take too seriously. You will leave knowing how to pick freestanding padlocks, but you probably won’t know how to pick open your front door. Getting really good at lockpicking, according to Thomas, takes a lot of practice and a ton of patience. A level one lockpicker, even one capable of busting out of handcuffs, probably wouldn’t have the know-how to break into anywhere valuable. “A novice lockpicker is more likely to break locks or picks. The practical applications are actually pretty limited,” Thomas admits. They might not even include actual thieving: “Crooks use bricks, not picks.”

Lockpicking might be especially undesirable in Virginia, where, unlike D.C. and Maryland, owning lock-picking equipment technically counts as intent to commit a crime. Although Pingor, a former law enforcement officer, says that law is rarely, if ever, invoked by police. Reassured by that knowledge, I head home to Fairfax, and browse Amazon for a set of picks.

Photos by Darrow Montgomery