She walks downstage, stares at the audience for a moment. Perhaps she is thinking and feeling, “It is your need for plays that is causing all this to happen, that is causing me all this pain. Are you happy now?” Then she exits.

—a stage direction from Will Eno’s The Flu Season

Will Eno’s plays can’t exist without an audience. And not just in the theoretical sense; the audience is written into the fabric of his scripts. The speakers in Eno’s numerous monologues intermittently beseech, interrogate, flirt with and apologize to the spectators. In the case of his Pulitzer-nominated solo show Thom Pain (based on nothing), a planted audience member conspicuously leaves the theatre not long into the show; and a real audience member is summoned on stage for an uncomfortable closing scene in which he is asked simply to stand upstage with his eyes closed.

The Brooklyn-based Eno will introduce his newest one-actor show, Title and Deed, May 8–June 3 at New York City’s Signature Theatre, where he is one of seven resident playwrights filling out the company’s first season in its shiny new building. This month Eno also debuts a new multicharacter drama, The Realistic Joneses, at Connecticut’s Yale Repertory Theatre (April 20–May 12). He’s been working simultaneously on the two plays for the past year.

“When I’m working on the monologue, I tend to put a huge amount of faith and trust in the audience,” he says, when asked whether the projects cross-pollinated. “People are pretty smart. It’s good to remember that fact when I’m working on The Realistic Joneses, which is more of a standard kind of play, one that fits more in the realistic tradition.” A basic ratio—that of audience members outnumbering performers—guides Eno’s writing to a surprising degree. “It’s interesting to think of a theatre with a play going on in it as one body, or one brain, and if someone says ‘gray house’ on stage, or ‘brook,’ or ‘animal,’ instantly there are all these connections and associations, and misfires too, going on back and forth all over the whole place,” he reflects. “If a play is really openly and honestly asking a question—a question it’s not really sure of the answer to—then the greater mass of people dealing with the questions will be in the audience.”

In more than one of Eno’s plays—including lesser-known monologues such as Lady Grey (in ever lower light) and Mr. Theatre Comes Home Different and in the short works collected in Oh, the Humanity and other good intentions—we see characters desperate to register, even in brief cameos, in someone else’s consciousness. They’re grateful to be pictured in their private moments doing something as ordinary as drinking a glass of milk, or as extreme as being attacked by a swarm of bees (a fate that pops up in two separate Eno works).

In Eno’s short play Intermission, and again in a fictional “intermission” scene in his Horton Foote Prize–winning Middletown, he experiments with scripting this connection across the footlights, having actors portray patrons. But according to the playwright’s own mathematics, the effect is vastly multiplied when the character can get us, the actual audience, to create those mental pictures, fill in those blanks.

When a play is successful and we do that in our seats in a dark theatre, it’s called engaging our imagination. When we do it in real life, for one another, it’s called empathy. If we can come away from a Will Eno play with an aftertaste of hope—after spending time with his fumbling, crestfallen characters, hearing their bleak histories and awkward conversations—it must be a by-product of flexing our empathy. Eno’s chicken soup for the soul arrives at your table in a chipped bowl with a big fat fly floating on the surface. But maybe that’s why he gets away with writing so sincerely about the value of kindness and compassion.

Eno’s chicken soup for the soul arrives at your table in a chipped bowl with a big fat fly floating on the surface.

A good laugh every now and then doesn’t hurt, either. “He has great wit and surprising perspectives,” says Les Waters, who directed the U.S. premiere of Eno’s Tragedy: a tragedy at California’s Berkeley Repertory Theatre in 2008, as well as Steppenwolf Theatre Company of Chicago’s 2011 production of Middletown, a play Waters describes as “terribly funny and deeply moving.” That play, which premiered the previous year at New York City’s Vineyard Theatre under Ken Rus Schmoll’s direction, is scheduled for another outing this coming September and October at Austin’s Hyde Park Theatre.

Artistic director Ken Webster, who will helm Hyde Park’s production of Middletown, says his theatre specializes in “dark comedies.” So it might seem odd that when Webster first discovered Eno’s writing in 2007, he decided to direct himself in Thom Pain after reading it aloud to his wife: “She started crying and begged me to stop.”

Okay, maybe the humor isn’t what hits you first. Middletown’s laughs don’t always read like comedy on the page:

TOUR GUIDE: I haven’t traveled, ever. I’ll walk around town, is about it. I’ll notice a building or something, “Hey, was that always here?” Main Street, Elm Street. I look at people and try to figure out their story. You can sort of guess the first and last facts, but for the rest I’m just kind of, “What’s going on inside of you?, because I have no idea.” I don’t know. I grew up here. I thought this was the world.

MALE TOURIST: Of course you did. But, hey, let me get a quick picture of you being wrong. (He snaps a photo of Tour Guide.)

FEMALE TOURIST: We always sort of want something more, I guess because there’s a long history of death in both our families. I guess we like things that are potentially monumental, but that aren’t necessarily monumentalized, yet.

In many cases, the humor comes from the sheer ineptitude of language:

JOHN DODGE: Time, you know. “Buzzzzzz.” “Plink.”

MRS. SWANSON: You said that the day we met.

JOHN DODGE: Something like it, I’m sure. It’s a theory of mine.

MRS. SWANSON: It’s not really a theory. You’re just making different sounds with your mouth.

JOHN DODGE: So are you.

MRS. SWANSON: True. “True.”

Eno’s work has earned him inevitable, if complimentary, references to predecessors. In a now-famous critical love note in the New York Times to Thom Pain’s 2005 Off-Broadway debut (a production that debuted in the U.K., directed by Hal Brooks and starring James Urbaniak), a giddy Charles Isherwood dubbed him “a Samuel Beckett for the Jon Stewart generation.” Middletown, which juxtaposes its small-town view with awestruck gazes toward the cosmos, has drawn comparisons to Our Town. But when asked to describe Eno’s plays, Les Waters simply says, “They’re like Will, really.”

In fact, an e-mail from Will Eno to a journalist sounds much like a monologue from a Will Eno play. Take his explanation of Title and Deed, in which the speaker’s distinguishing characteristic is that he’s “not from here.” (The role will be played at Signature by Conor Lovett under the direction of Lovett’s wife, Julie Hegarty Lovett; the pair are co-artistic directors of Gare St. Lazare Players Ireland.) Eno writes: “The guy is more like me than I thought he was going to be…The thing started as a kind of psychologized treatment of a philosophical idea, but it’s become something much more simple. You know when you’re a kid, and, for a moment, suddenly, everyone seems really weird, things just seem weird? Like, life is just mumbling going on in another room, or something? This is sort of that.”

And here’s Eno on The Realistic Joneses, to be directed at Yale by Sam Gold. The play was originally advertised as being about neighboring couples living in identical suburban homes, but, he writes, “Their houses aren’t identical. I made a small change there. They’re close, though. I think, in a funny way, when you see houses that are similar, like in a development, you maybe tend to think more of the people inside as representatives of real and raw and actual humanness. Or not as representatives, but, just, people, humans. Whereas, when you see houses next door to each other that are each tricked out in some particular and idiosyncratic way, with flower boxes and flags and bird feeders, you just tend to think of which particular traits are expressed, and what the people who live there might look like. But plain and identical houses, or apartments, you tend more to think, ‘There are human beings in there, and they are eating and sleeping and making love and working.’ And you think, ‘What are human beings like?’ Rather than, ‘What are these particular people like?’”

In keeping with this universal line of inquiry, Eno’s plays have open-ended settings. The Flu Season occurs “in a mental health institution of a not very specific type.” For all we know, Middletown could be in Ohio, Arizona or New Hampshire. Tragedy: a tragedy follow a live news broadcast of an unnamed disaster, which may be affecting a single anonymous city, or perhaps the entire planet.

According to Antje Ellermann, who created the sets for Waters’s productions of Tragedy and Middletown, this poses certain challenges for a designer. “For Middletown I rounded up a lot of research of small American towns and then distilled it down to what seemed most common and iconic,” she says. For Tragedy, on the other hand, “a TV studio is an inherently surreal world,” she notes. “We discussed the backdrop right behind the news anchor, looking at maps of the world and searching for the most unrecognizable or generic skylines. In the end we settled on a plain blue glowing cyc.” She adds, “Each time I worked with Les on a Will Eno play, I have been initially inspired by how philosophical and existential it is, and I have looked each time at depictions of the universe and solar systems, only to return to much more literal ideas, such as a house, steps, grass, etc.”

“I actually think Will’s plays are incredibly specific, and demand incredibly realistic details,” declares another scenic designer, David Zinn, who worked on Middletown at the Vineyard and is now tackling The Realistic Joneses at Yale. “Will’s plays are a collision of the familiar and strange, or the tipping point from canny to uncanny,” he says. “I think of his plays as a kind of series of close-up photos, where the actors are foregrounded and the background tends to be a bit of a blur. I guess the blur is the hard part, but just because it’s blurry doesn’t mean it’s not specific.”

When Youngblood Theatre Company of Milwaukee staged The Flu Season last month, its creative team went truly specific: site-specific, that is, building a stage within the cafeteria of a local hospital. “The play does a great deal of messing with expectations and setting up conventions, only to completely abandon them or call attention to them when the audience least expects it,” says artistic director Michael Cotey. “When we perform in a found space, we inherently mess with audience expectations.” A pivotal gesture in Youngblood’s show was not in the script: A dying character rises from her bed and departs the world of the play—and the theatre itself, exiting into the cold Wisconsin night.

Eno’s upbringing may hold a clue to all this geographic ambivalence. “I grew up in a house that my dad bought from the Commonwealth of Massachusetts for a dollar, because it had to be moved, because a highway was being built. So they moved it and rebuilt it in this different town and it looked old and it was cold inside, and of all the things my parents would never do again, that was definitely one.” He adds, “In some funny way, I feel as if I grew up in an unspecified location. Like, if I look at a map of the United States, and put a dot where I grew up, I’m always surprised at where the dot is.”

He goes on to confess, “I’ve felt inspired to write about a specific place, maybe Maine or Vermont or even Norway, but I never have done it. In some way, it has never felt right, because to do that is to at least partly say, ‘This thing takes place here, and therefore the people in it are thus.’”

Bumper stickers and fridge magnets would have us believe that life is what happens while we’re making other plans. In Eno’s world (and, let’s face it, in ours), life is not only everything that happens but also what doesn’t happen.

Take the mechanic in Middletown who breaks the fourth wall to confide:

I had ideas about getting famous, getting on local TV with my meteorite. When it turned out to just be a rock, I thought I could still make some headlines with it if I threw it off a bridge, hit some family in their car and killed everybody. But then I figured, you know what, forget it, that’s not me. So now some family’s driving around, not knowing how lucky they are, not knowing how sweet it all is.

It’s true that most Eno characters discover making plans is a futile exercise. When a Middletown character resolves to die and does so a handful of pages later, it’s no tragic mission accomplished; in the interim his intentions have been foiled not once but twice, and his death is regrettable, and a bit embarrassing, and full of “what ifs” and “if onlys.” Not that we’re left to wallow in regrets, since he dies across the stage from a birth in the same hospital. Eno has said in a past interview that this juxtaposition of ending and beginning was the seed of the play.

Eno has toyed with the unexpected placement of bookends before, nowhere more startlingly than in The Flu Season, which features narrators named Prologue and Epilogue. At first, Prologue is upbeat, eager to follow the plot; he remains unaware of Epilogue’s presence. Epilogue is cynical and weary; but he proves, within his hindsight, also to be—yes—empathetic. He pities Prologue, not to mention the hapless playwright who keeps trying to sort out this tale.

There is a moment when Prologue falters, shocked by a turn of events. Gently, Epilogue breaks in with advice for us all:

Stop crying. Practice holding and kissing your pillow, for when the day comes you really need to hold and kiss it…Everything is worse, including our desire for improvement. Of a life, a life story, a play. All are awful, worse, the same, but, in the end, to be lived with. Life is fine.