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Actor/writer/director/producer Jake Lipman ’00 founded Tongue in Cheek Theater Productions in 2006.

How do women navigate today’s workplace in a world where gender is still an issue, gray areas abound, blatant harassment exists, the glass ceiling has not been completely shattered and, to top it off, you are expected to maintain a healthy work/life balance?

Those were the questions actor/writer/producer Jake Lipman ’00 sought to address with her new play Relentlessly Pleasant. “I wanted to create a play that looked at women in the workplace and saw some hope for our future,” she says.

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Lipman hopes to use “Relentlessly Pleasant” as a corporate workplace behavior training tool.

Relentlessly Pleasant, written and directed by Lipman, takes place on the hectic day before a new, all-female coworking space launches. The office experiences a series of unforeseen conflicts and calamities—everything from a #MeToo incident to various power dynamics among the staff.

Lipman’s company, Tongue in Cheek Theater Productions (TIC), also produced the play, which ran in New York’s Theatre 54 at Shelter Studios in October. A reviewer for Onstage Blog wrote, “[Relentlessly Pleasant] does a very fine job at exploring issues of sexual harassment, and what it means to be a feminist in 2018, on a very human level, and does so with an excellent balance of both light humor and potent drama.”

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Shauna Pinkett and Jessica DiSalvo in “Relentlessly Pleasant” produced by Tongue in Cheek Theater Productions, in New York City October 2018.

Though its debut run is over, Lipman wants to give small independent theater companies and college theater departments (especially at women’s colleges) the chance to perform Relentlessly Pleasant, and she is adapting it for television. She also sees the play as a teaching tool for corporate America that could be used to start conversations on workplace behavior.

“By showing how eight distinct women interact at work, we are showing women many different ways to accomplish their goals,” says Lipman. “No one character is flawless or ideal, but that’s OK. We all must find our way, and know that we’ll make mistakes, but we can improve and get ahead, not just in spite of, but because of our foibles.”

Lipman founded TIC in 2006 to produce plays that interested her as a performer. Over 13 years and 40 productions, Lipman’s goal has evolved to writing and producing thought-provoking, topical theater that teaches and entertains—a perfect approach for the former Smith theatre major.


In the video above, Jake Lipman ’00 talks more about why she wrote Relentlessly Pleasant.

“Smith has played an enormous role in my development as a person, as a feminist, and as an artist,” says Lipman. “After writing Relentlessly Pleasant, which has eight female characters and one male character, I had a meeting with one of my female actors. She remarked that she was surprised at how great the dynamic was in rehearsal, when it was just women in the room. I said, ‘Yeah, that’s what happens in an all-female environment. It becomes about who the people are, not about their gender.’”