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Orlando Theatre Review

Reviews and reflections of all aspects of live theatre in Central Florida

Review: “My Dear Debbie” at New Generation Theatrical

Ilana Jael, February 19, 2026

Unlikely as it sounds, fans of lighthearted retro sitcoms and dark theatrical dramas will both probably be satisfied by New Generation Theatrical’s current production of My Dear Debbie. Thematically, it’s a huge departure from the last show of the company’s I had a chance to review even as it follows the same basic formula: two intermissions, playful audience-interaction interludes, and even the mid-show delivery of some complimentary alcohol. 

But where Gothic Castle was genuinely just after laughs, the surface frivolity of My Dear Debbie is only a thin veneer over its deeply unsettling story. A far more ambitious piece written and directed by Casey Tregeagle, it also emerges as a more interesting and moving one, if also one that suffers more for its structural weaknesses. 

Even during a seemingly upbeat introduction by Hannah McGinley Lemasters as Studio Host establishing the show’s setting and premise, you can sense a subtle darkness under the surface. We are, according to her, there to serve as audience members for an in-studio taping of a sitcom that shares the play’s title. The in-universe version of My Dear Debbie ably mimics the structure of the TV shows it seeks to emulate, though its humor wasn’t particularly sharp otherwise. 

A scene at the end of the show’s first act brings the dark themes to the surface. From then on, we shift back and forth between the cheery world of the sitcom and studio to a bleaker one that is implied to have a connection to it. 

It isn’t too hard to figure out the basics of what’s going on, but I’ll still try to avoid spoiling any of the reveals too specifically. To give you an idea of the territory, though, I can point you towards the show’s content warning: 

Please be advised that this piece has themes of domestic abuse, sexual abuse, and child sexual abuse, as well as violence and mature language and content. Viewer discretion is advised.

I’m not the type of theatregoer to be put off by such subject matter, and in fact found the boldness of the show’s conceptual and emotional risks to be genuinely enthralling. But though the extremity of the tonal shifts was clearly deliberate, it did sometimes feel so jarring as to interfere with my investment in the story as a story as opposed to as a conceit. I have no problem with how far the play is willing to go, but I did find myself having to mentally leap over unbelievable details, sketchy character motivations, and unclear internal logic in order to buy in enough to feel the full weight of the play’s devastating conclusion. 

In other words, Tregeagle’s script seems to fall a few edits short of its full potential. As its director, though, he’s also responsible for camouflaging many of these structural weaknesses with his expert shaping of the piece. His staging makes full use of New Gen’s unique and expansive theatre space, and his cast excels at managing the multifacetedness of the challenging material. 

It’s a well-rounded ensemble piece that gives supporting cast members Lemasters, Beth-Ann Stripling, Eric Sharp, Alex Mrazek, Carly Clark, River Banks, and Michael Knight almost as much to chew on as leading lady Taylor Byerly, who does a fine job with the play’s most difficult role.

Tregeagle is also credited as sound designer, and here his abilities do some superb scene setting work. Not only was every actor always audible and every laugh track and crowd noise cue deployed seamlessly, he creates subtle soundscapes that help clarify the show’s worlds even as they begin to bleed into one another. 

Last but not least among Tregeagle’s credits is for his costume design, which featured vibrant, evocative, and period appropriate attire and called for some impressive quick changes. He’s aided in visually differentiating these worlds by the work of Lighting and Set Fixtures designer Michael Darby and set decorator Michael Knight. 

All in all, I was pretty impressed by how well New Generation executed My Dear Debbie, which effectively ensured that I was engaged and entertained by the piece even during the points where the script itself was underwhelming. As someone who sees quite a lot of theatre, this show also felt like something stylistically and narratively different than anything I’ve ever seen before—which, for me, was a huge point in its favor. 

In other words, My Dear Debbie has a lot more going for it than corny jokes and a free shot—though if those sound like reasons that you’d want to buy a ticket, by all means go ahead! The show will be running for only three more performances from February 20th to 22nd, and it’s one that adventurous local theatregoers definitely won’t want to miss. 

REMAINING PERFORMANCES AND TICKET INFO:

Performances at New Generation Theatrical Studio at 3201 E Colonial Dr Orlando, FL 32803 on:

February 20th, 8:00 pm

February 21st, 8:00 pm

February 22nd, 2:00 pm

Tickets available here for $25.

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