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A rebel and her ‘Romance Novels’
Playwright Boo Killebrew (center) with actors Justin Long and Mary Wiseman of “Romance Novels for Dummies.’’ (Steven G. Smith for The Boston Globe)
Justin Long and Mary Wiseman in rehearsal for “Romance Novels for Dummies.’’ (Steven G. Smith for The Boston Globe)
By Christopher Wallenberg
Globe Correspondent

Romance Novels for Dummies

Presented by the Williamstown Theatre Festival, July 20-31. At the Main Stage, '62 Center for Theatre and Dance, Williamstown.

Tickets: $40-$68; 413-597-3400; www.wtfestival.org

WILLIAMSTOWN — Ever since Boo Killebrew was a little girl growing up in Gulfport, Miss., she’s rebelled against traditional gender roles and conventional notions of femininity. When she and her friends would play dress-up and put on fake weddings, she never wanted to be the beautiful bride with the flowing white gown. Instead, she says, “I wanted to play the drunk grandmother.’’ Even at that young age, Killebrew's offbeat sense of humor was beginning to show.

Despite Killebrew's youthful renunciation of gender roles, she feels that the two sisters at the center of her play “Romance Novels for Dummies’’ actually represent “two different sides of myself.’’

The stage comedy, which receives its world premiere at the Williamstown Theatre Festival July 20-31, marks a watershed work for Killebrew, 35, a Boston University graduate who has been toiling on the fringes of the downtown New York scene for years.

In the play, the central character, Liz (Mary Wiseman), is a 29-year-old, well-mannered stay-at-home mom who has married her high school sweetheart and is raising a 6-year-old daughter. Her sister Bernie (Ashley Austin Morris) older by three years, is more of a wild child. An aspiring actress, she smokes, drinks, swears like a truck driver, and is living an unabashedly single-girl life in New York City chock-full of late-night revelry and hazy one-night stands.

Like Bernie, Killebrew is lively, animated, and bawdy. She says she was always attracted to a bohemian life. That’s why at the age of 18, Killebrew followed her dream and left the South to study theater at BU.

“Bernie surrounds herself with misfits and people who are outsiders, and I feel like I do that in my life. I love Mississippi, but I did feel like an outsider,’’ says Killebrew, in her honey-dipped twang. “She also has this sense of abandon. She’s a free spirit. But I think she’s very nurturing at the same time, and I’m a caretaker 100 percent.’’

While Liz and Bernie have different personalities, priorities, and approaches to life, it’s clear they love each other deeply and share important things in common, including their Mississippi roots and an irreverent sense of humor spiked with a dollop of Southern sass.

As the play begins, Liz has fled her hometown of Holly Grove after the sudden death of her husband to go live with her sister in New York. With Bernie’s help, she’s raising her precocious daughter, Lily, in a Brooklyn brownstone purchased by Liz’s big-hearted but tradition-bound in-laws. But the sisters don’t always see eye-to-eye on child-rearing or navigating the grief that Liz is stoically suffering.

The relationship between Liz and Bernie reflects aspects of Killebrew's own dynamic with her real-life older sister, Bette, who lives in Oxford, Miss., and is a working mom with a husband and two kids. “On paper, we could not be more different,’’ Killebrew says. “But our hearts have the same landscape, our beliefs are the same, and our sense of humor is the same.’’

As Liz expresses an increasing fascination with the formulaic setups, plot devices, and facile happily-ever-afters of romance novels, Bernie tells her that the books won’t be able to keep her warm at night, and she urges her sister to try out Internet dating so she can at least get her “freak on.’’ So Liz embarks on a series of dates with three very different guys (all played by Justin Long). While the encounters take her out of her grief for a moment and give her a glimpse of a possible future, they also throw her off balance.

“I was interested in what happens when you follow this standard narrative that you’re fed, which is happiness equals getting married and having a child and a family,’’ Killebrew says. “But if you follow that formula and then the rug gets pulled out from under you, what happens?’’

Then there’s the other side of the coin, which Killebrew says offers an equally limiting perspective: “If you don’t have the impulse to start a family, you can follow the standard narrative of the Single Woman’s Quest, where it’s like, ‘She doesn’t need a man. She doesn’t need a family. She’s got her career and her life.’ ’’

Wiseman, who met Killebrew when they were both studying at Juilliard (Killebrew recently finished the playwrighting program there), explains that Liz can’t “access or process her deep wells of grief, because she wants to be good and bright and bubbly for her daughter. But holding on to all of those bad feelings and those fears and tamping that grief down can be dangerous, because it will eventually explode.’’

Wiseman believes that Killebrew's perspective as a writer can be traced to the tension between her genteel Southern upbringing and her free-spirited soul. “There’s a real intense thing about manners in the South, a real prescribed way to be a woman,’’ Wiseman says. “Boo grew up with those expectations, so she’s generous and kind and polite. But then she also can really cut loose and be searingly honest and raunchy and funny and hold her own with anyone.’’

At Boston University, Killebrew cofounded an ensemble-driven theater company, Collaboration Town, with a group of like-minded fellow theater students. After graduation, they moved to Brooklyn and spent the next decade making devised theater that’s been produced at various downtown and off-off-Broadway venues. Killebrew acted in many of those shows, which include “Family Play (1979-Present),’’ “The Deepest Play Ever,’’ and “The Momentum,’’ which won a NYC Fringe Festival Excellence Award and earned a GLAAD Media Award nomination. Killebrew says the company, 13 years old now, has become a “creative safe haven.’’

“To be able to be that playful with a group of people, to be able to take risks like that and fall down with a safety net is really great and hard to come by,’’ Killebrew says. “We also challenge each other constantly. It feels like we share this engine of curiosity and fuel each other’s experimentation.’’

Moritz von Stuelpnagel, who’s directing “Romance Novels for Dummies,’’ met Killebrew when they were both students at BU, so he’s familiar with her evolution as a writer. “The boisterousness and the buoyancy of Boo as a human being, even in the face of the challenges that life throws at you, is so utterly present in this play,’’ he says.

He points out that these kinds of candid, unvarnished stories about young women, with frank discussions of sex and love, are still unusual to see in the theater, even though they’re cropping up more in television series like “Girls’’ and “Broad City.’’

“The fact that Boo puts women at the center of this play and lets them be funny and lets them be honest about their sexuality and the way they feel about relationships is in some ways revolutionary.’’

Romance Novels for Dummies

Presented by the Williamstown Theatre Festival, July 20-31. At the Main Stage, '62 Center for Theatre and Dance, Williamstown, Mass. Tickets: $40-$68; 413-597-3400; www.wtfestival.org

Christopher Wallenberg can be reached at chriswallenberg@ gmail.com.