It takes a while, but Lipez and her director, Thomas Kail, manage to concoct a fascinating study of three intricate and toxic personalities at the crucial crossroads of life and technology. It's 2007, and Toby (Keith Nobbs), Joe (Matt Dellapina), and Heidi (Aubrey Dollar) are former college buddies who've spent the last few years since graduation collaborating on a social network called Joinme2u.com. Alas, because of another little site that launched around the same time as theirs, called Facebook (though use of that word is strictly verboten in the apartment/office the trio shares), they've never found the success, money, or even satisfaction they once seemed guaranteed. This has led Toby and Joe to take side jobs as tutors to well-off families (in no small part to fill a deeper well of funds for their site), and Heidi to make ends meet editing college admissions essays.
The irony, though, is that these people who are attempting to establish their careers by bringing (and keeping) people together to each other are completely unable to keep their own social circles in check. Toby has been not so secretly in love with Joe for ages; Heidi has been fantasizing for the last month about the Asian man named Kwan whose essay she tweaked; and Joe has run afoul of one of his most prominent clients, the especially spoiled 17-year-old Milo (Chris Perfetti), who's now working with Toby and apparently as unable to keep his mouth or his ears shut as he is his brain open.
It's just before intermission that the tension hits critical mass, with Joe and Toby bonding a little too securely over their shared frustrations at Milo and Heidi, and Joe succumbing to a dangerous sense of obligation that promises to give Toby exactly what he's long wanted most. Dellapina's easygoing affability, bearing just a few darkly unpredictable edges, blends beautifully with Nobbs's nervous, oddly innocent neuroticism to create what is, within this world's reality, a thoroughly believable, if violently symbiotic, partnership.
Once the explosives are laid, Lipez can spend most of the second act exploring how each of the characters reacts to their ignition. As long as she focuses on the complexities between the group's work and the way they react with each other, the play is frequently taut and thoroughly involving, stripping everyone of the illusions they've erected to protect their innermost selves in a world that's demanding ever more public engagement.
Unfortunately, Lipez spends far too much time building too narrow a foundation to support everything she attempts to construct. The first three-quarters or so of Act I are tired and tedious, consumed with minutiae that convey no energy or invention. Perhaps the nuts-and-bolts discussions of the website's mechanics and the men's tutoring gig are vital, but as rendered here they barely qualify as dramatic. And the border to the legitimately unbearable is crossed when the characters start elucidating at unthinkable length on exactly how Heidi's non-romance with Kwan (Louis Ozawa Changchien) functions.
The Tutors reaches no lower point, but during that chunk of the story it struggles to rise much higher. Changchien is neither mysterious nor appealing enough to elevate the schematic Kwan (in either real or imagined form), and so even at his most winning — when Kwan and Heidi honestly connect for the first time — he feels shoehorned into the action. Dollar invests Heidi with an alluring and natural quirkiness that provides a supple contrast for the men's lower-key attitudes, but it's not sufficient to link dots that Lipez didn't bother to provide. And though Perfetti injects Milo with a palpable neediness that burns through his façade of rickety swagger, the character is just too unlikable to register as more than a device.
But Toby, Joe, Nobbs, and Dellapina make an unbeatable combination, and keep you hooked during the moments where everything else doesn't quite hang together. They establish a charming intimacy together that's reflected in everything from Kail's tight direction to Rachel Hauck's precisely sloppy apartment set design, and really reinforces the links that men form between each other when faced with unusual and trying circumstances.
At each step along the way, as you watch them trying to hold together something that's all but visibly desperate to fall apart, you sense the importance that unites them: Each needs to need the other, and to be needed by him. Admittedly, not quite in the same way. But Toby and Joe discover (in several ways, most of them hard) the truthfulness of the old cliché that the devil is in the details. Both they and The Tutors are never better than when they mine those details for all they're worth.