Cast and Creative Team Set For Ken Ludwig’s DEAR JACK, DEAR LOUISE at Gulfshore Playhouse

The cast and creative team have ben announced for Ken Ludwig's Dear Jack, Dear Louise, a heartwarming World War II love story written by Tony Award-winning playwright Ken Ludwig, inspired by the true courtship of his own parents and the results are anything but expected. Performances run March 24 - April 26, 2026, with Opening Night on Thursday, March 26, in the Struthers Studio.

Dear Jack, Dear Louise follows two strangers, a military doctor and an aspiring actress,  who meet not in person but by letter during World War II. Their long-distance correspondence becomes a joyous, comedic, and deeply personal love story that spans years of uncertainty and longing. 

The cast includes:

Pete Winfrey (as Jack) is a NYC based actor originally from St. Louis who is thrilled to be making his Gulfshore Playhouse debut telling this story for the second time with this creative team. Favorite regional theatre credits include Waitress (Saugatuck Center for the Arts), Midsummer Night's Dream (Alabama Shakespeare Festival), and Twelfth Night (Shakespeare Festival St. Louis). He's also appeared in film and tv projects including “The Gilded Age.” 

Oriana Lada (as Louise), is a NYC based actress and singer who is excited to be making her Gulfshore Playhouse debut. NYC credits include: Clubbed Thumb, New York Musical Theatre Festival, Notch Theatre Company. Regional: Repertory Theatre of St. Louis, Alabama Shakespeare Festival, Trinity Repertory Company, New Jersey Repertory Company, The New Harmony Project, Great River Shakespeare Festival. 

About the Creative Team

Tony Award winner Ken Ludwig (Playwright) is regarded as the most performed playwright of his generation. The playwright behind classics like Lend Me a Tenor, Moon Over Buffalo, Leading Ladies, and The Fox on the Fairway, he has had six productions on Broadway and eight in London's West End, and many have become standards of the American repertoire.

The creative team for Dear Jack, Dear Louise is led by Risa Brainin, who is directing this heartfelt play. Risa is a freelance director and Founder/Artistic Director of LAUNCH PAD at the University of California, Santa Barbara, who returns to Gulfshore Playhouse after directing Every Brilliant Thing last season, which starred Jeffrey Binder. She has held artistic leadership roles with organizations including the Guthrie Theater, Shakespeare Santa Cruz, Kansas City Repertory Theatre, and Indiana Repertory Theatre. At Risa's side is Assistant Director/Dramaturg Matt Lytle, a New York-based director, dramaturg, actor, and acting coach who is delighted to make his Gulfshore Playhouse debut. Matt has contributed extensive dramaturgical research to ensure the historical accuracy and context of this production.

The creative team for Dear Jack, Dear Louise also includes Scenic Designer Sara Ryung Clement, who is creating a design for the Struthers Studio's in-the-round staging, with seating on all four sides of the black box theatre; Costume Designer Devon Painter, whose work helps define the characters and period; Lighting Designer Michael Klaers, who shapes the mood and atmosphere through light; and Sound Designer Vincent Olivieri, who creates the production's auditory landscape with support from his assistant, Melanie Falcon. The production is stage managed by Kelli Karen, who oversees rehearsals and performances to ensure the show runs seamlessly, and casting is by Michael Cassara, CSA, known for his extensive Broadway and regional work. 

“We're honored to bring this moving and personal story to life on our stage,” said Kristen Coury. “Ken Ludwig's blend of humor, warmth, and heartfelt emotion resonates deeply, and this cast and design team beautifully realize that spirit.”