Dear Jack, Dear Louise: the Greatest Generation in Letters
Last night we enjoyed a play at the Majestic Theater that took us back to the days when letter writing was everything. It was a time when the word ass was abashed, and it was abbreviated as ‘the A Word.’
The year was 1942, and World War II was the most important thing in the world. In this play with just two characters, we hear the actors Jack and Louise read and respond to letters they wrote to each other…but they are two strangers. With Jack (Gregory Boover) on the army base in Medford, Oregon, and Louise (Alexandra O’Halloran) in her apartment in Brooklyn, their fathers suggested in the play’s beginning that they might enjoy writing to each other during wartime.
They’ve never met, but soon they bond over the thousands of letters they exchange in a world without FaceTime, email, or even a way to talk on a telephone. Pure heaven, to many of us, as some can still remember the importance of letters and having to capture someone’s tone, attitude, and mood all from the words they scribbled.
I can personally relate to this play, as I once had a pen pal I didn’t know, but with whom I ended up having a four-year epistolary relationship. There is something so powerful about exchanging letters that millions of fans of The Correspondent are hungry for more from best-selling author Virginia Evans. The book has been a huge bestseller in 2025, sparking a letter-writing revival and thousands of book clubs sharing the read.
The Majestic set is cleverly split in two—a soldier’s barracks on one side, a woman’s bedroom on the other—letting us watch their parallel lives unfold even as the story keeps them far apart. This play keeps things moving even with dialogue that sometimes seems more like a phone call than a handwritten missive.
I enjoyed the scene where Louise plays two roles, popping over to be one actor and then back to herself, while she performs a scene from Arsenic and Old Lace. She’s determined to make it big on Broadway, and after many auditions and tears, she lands a role in a touring production of a Broadway play.
Jack, in his barracks, tending to the wounded, worries about the inevitable day that he will be shipped out overseas to where the war is raging. But in the time between, he hopes and prays he can line up leave to see Louise in person. Their passion is obvious from the tone of the letters; they are both eager to move to face-to-face, but so many things stand in their way.
And the first one is that new gig. As happy as Louise is to score the big role, it throws out the chance to meet Jack on the five days of leave he has secured. Oh, drat, she’s going to be performing in Cincinnati.
Louise is visiting her family and chances on the opportunity to meet Jack’s family, but not Jack. He’s hesitant; he’d rather have her meet them when he’s there and says no. But minutes later, she’s writing to tell him how much she enjoyed meeting his mom and her very nosy eleven sisters, full of questions, of course.
The story progresses, and the bombs get closer to Jack, as he hides beneath his bunk at the crack of an explosion. We fear they might never meet, and they, too, don’t know what will happen to their epistolary life… will it blossom into real life?
This show is full of surprises, and these two Equity actors shine through the whole production. This is an inspiring and very on-trend show, one worth seeing live, not on a screen.
Dear Jack, Dear Louise, written by Ken Ludwig, directed by Sue Dziura, with Gregory Boover and Alexandra O’Halloran, both equity actors in the two roles. At the Majestic Theater, Elm St., West Springfield. Tickets are $35-$38 and can be purchased by calling the box office at 413.747.7797 or going online here.