Fragile, ephemeral moments that define the trajectory of a person’s life can happen in a whisper or with the impulsivity of youth, and sometimes only the wisdom of time and reflection reveal their significance.

The Florida Repertory Theatre’s production of “Bloomsday,” the poetically poignant play by acclaimed playwright Steven Dietz, explores the confluence of memory and the passage of time, regret, loss and the endurance of love throughout the years.

Inspired by the holiday of the same name that is celebrated annually on June 16 to honor the life and literary contributions of Irish author James Joyce, “Bloomsday” is named after Leopold Bloom, the protagonist in Joyce’s famous literary masterpiece, “Ulysses.”

The play is set in Dublin, Ireland, and nestled in the juxtaposition of the city’s modern vibrancy and timeless remnants of cobbled streets and Georgian architecture that connect the past and the present. In a way uniquely suited for live theater, the action navigates fluidly back and forth between the present and a brief chance encounter between characters Robert and Caithleen 35 years prior.

The fundamental language of theater

For Dietz, the play holds special meaning and was born of a time in his life marked by vulnerability, raw emotion and reflection.

“It’s a play about a man trying to go back to a time and a place, and in the magic of the theater, he succeeds. It’s a play about maturity, and it’s a play about innocence,” Dietz said. “It’s a play I’m very proud of. It’s a play that’s had a good and busy life and won some awards, which I’m very grateful for.

“(‘Bloomsday’) was written in a period when my kids were teenagers. My wife and I both just lost our mothers, so there was a great amount of grief, watching our kids get older, and then we took a trip to Ireland. Sometimes, you take a trip, as you know, at exactly the right moment.”

“Bloomsday” is the second play by Dietz to be commissioned by Naples’s residents Charles and Benita Staadecker.

“They commissioned ‘Becky’s New Car,’ which is probably my most produced play that’s not an adaptation,” Dietz said. “And then they and a few other couples in Seattle came together again and commissioned ‘Bloomsday.’ They put money forward to the theater to pay for the theater’s ability to hire me. I was not given any strictures of story or theme or anything, and I picked the stories of those plays.”

Much like the characters in his play, a chance encounter and experiences on his family’s trip to Dublin in the wake of his mother and mother-in-law’s deaths sparked the idea for what Dietz would later craft into “Bloomsday.” On the plane ride to Ireland, he read “Ulysses” for the first time on his computer and decided to purchase a hard copy of the book while on vacation.

“I had never read ‘Ulysses,’ and I just kind of dipped into it as we traveled in Ireland,” Dietz added. “I just kind of essentially read it as poetry, which is, I think, the fundamental way to try to read ‘Ulysses.’ I certainly didn’t get through all of it, but certain moments of it were really potent with me. One day in Dublin, I was getting a copy, and as I was waiting in line, I saw this young man come up and he plopped this massive paperback copy of ‘Ulysses’ on the counter next to him, and he ordered a copy.

“I struck up a conversation with him, and I asked him what he was doing, and he said, ‘I lead tours of this book.’ The book itself is a man walking around Dublin for one day of his life,” Dietz continued. “This tour guide was taking people on the tour of the places in the novel. That notion stuck with me, and I thought, ‘There’s got to be something in a man or a woman giving a tour and someone going on that tour and seeing Dublin when they’re older and knowing that something formative happened to them when they were younger. And that, like anything as a writer, it sticks in your head, and you go, ‘God, what a good idea.’”

At times, a tender and almost mystical meditation, “Bloomsday” also has moments of wit and comedy that promise to captivate audiences.

“I think the theater’s fundamental language is poetry. When I say that, it’s not flowers and light and moonbeams. What I mean is more meaning and less time,” Dietz said.

“In the great spirit of the Irish, the place thinks like a comedy, and I’m sure the production will bring that out because the Irish people do that sense of humor side by side with that sense of ache so perfectly. I’m just doing my best to ride that Irish wave. The thing I love about the theater is that we get to have characters who have that line right when they need it. I imagine an audience that wants that wants eloquence, and I imagine an audience that wants to be delighted and entertained,” reflected Dietz.

Four actors portray the younger and older versions of Robert and Caithleen in the production, allowing audiences to witness beautiful moments of interaction between characters in various stages of maturity — including between their younger and older selves.

Professional actor Braydie Aldrich portrays Robert as a young man. After a recent breakup and an impromptu trip to Ireland on Bloomsday, he stumbles upon Caithleen, a young woman who is leading a Bloomsday tour around the city of Dublin.

“My character is Robbie, and he’s 20. He’s an American boy from Seattle, and he had a trip to go to London with his girlfriend, but then he and his girlfriend broke up because she didn’t think that Robbie was serious,” Aldrich said. “He doesn’t want to go to London anymore, and he’s like, ‘What’s Dublin like?’ So he goes, he gets a little lost, and he ends up seeing this really beautiful girl. He’s really taken aback by her and enthralled just with the way she speaks and her beauty and everything about her. But he messes up along the way. He’s really relatable. I love this character because I feel so close to him because we’re around the same age, and I’ve had some similar experiences.”

The role of young Caithleen is played by Jessica Mosher, a Canadian actress and award-winning writer based in New York City. Mosher explained that Caithleen leads with her heart and is headstrong and impulsive. As an actress, Mosher relished the opportunity to explore the craft of highlighting the similarities between younger and older versions of her character.

“I love this character. I get to work with another actor, the wonderful Lynn Hawley, to figure out how we create similarities between the younger version of her and the older version of her,” Mosher said. “It’s this interesting creative process where we’re not just developing this character on our own and making choices unilaterally about who she is and how she moves to the world, but we get to sort of build that with another person, which I think is really precious.

“I also think it’s fascinating to sort of determine the ways in which our Caithleen and our Cait are the same, like, sort of the indelible human pieces of her that remain through time, but also the ways in which we change over the 35-year age gap between us. I think that’s one of the most special things about this play.”

Perfecting an Irish accent presented Mosher with a welcomed challenge and tool to convey authenticity and bring her character’s personality to life.

“A lot of it (preparing for performances) for me is the dialect — the trying to honor or do justice to a Dublin dialect and make sure that that is coming out as authentically as possible,” she said.

“Some actors will talk about finding the key to their character, whether that’s a physical stamp or an emotional connection to them, but for me, I really think a dialect is a really great key into a character. It’s a really good entry point because when you’re speaking in a different way than you normally do, you’re just not yourself, right?”

Connecticut-based actor Duke Lafoon portrays the older version of Robert who has traveled to Dublin 35 years after his serendipitous meeting with the young Caithleen to explore his regret over the lost opportunity to forge a lasting connection years ago.

“He has made a trip back to Dublin 35 years after he met a girl that just lit him up, and he was too scared to do anything about it,” Lafoon said. “He has held on to it in his heart for 35 years, and his life has gotten to a place where he’s ready to maybe explore those old regrets. So, he makes a trip back to Dublin to finally just have a lunch with this girl. Just meet her once again.

“At one point, (Caithleen) offers her hand to him; I couldn’t take it. I couldn’t do it. I was fearful and I was prideful, and I couldn’t do it. So, we left with a lot of things unspoken. It’s this beautiful play about lost opportunity and regret.”

Rehearsing for a production creates an intimate cohort that lends itself to fast friendships and meaningful connections between actors as they delve into the complexities of the script and the emotional lives of their characters.

“In this play, there’s a magical quality to it, and the language is a little heightened, especially when it’s talking about ‘Ulysses,’ which is this amazingly dense book to get through. I love the intimacy that you get when you work in the theater. You get to know people really fast. I look around and I see these faces, and I’m like, ‘I’m going to know you guys. You know, we’re all going to be best friends in a week,” Lafoon elaborated.

As the mature, older version of Cait, professional actress Lynn Hawley brings years of experience on Broadway and regional theater to her portrayal. She explained that the first days of rehearsal bring nervous energy and excitement to even the most seasoned performers.

“I love the director, Maureen Heffernan. She has us on our feet already,” Hawley said. “The second day of rehearsal, we were on our feet, which is so great for me because I’m very physical, and I need to be on my feet and try things and have it be just bloody awful in the beginning, just to get it out. And the accent — you can’t do it all at once, so you just sort of have to do it badly for a while. I’m just trying to be brave and get up and just throw it on the wall and see what comes out at this point.

“It is kind of magical. I just think it’s such a beautiful play to come see because you’re grappling with just enormous things like time and aging and regret, and then I’m on stage with my younger self. I’m looking at myself younger, and just the idea of that blows your mind,” she said.

Combining longing with humor, “Bloomsday” explores the poetic beauty of fleeting moments and the weight of choices left behind. Audiences are invited to share this poignant exploration of how memory and love evolve and defy the constraints of time in the production of “Bloomsday” at Florida Rep. ¦

In the KNOW

“Bloomsday”

· When: Now through March 2, 2025

· Where: Artstage Studio Theatre, 2267 Bay St., Fort Myers

· Tickets: Prices start at $67

· Info: floridarep.org or 239-332-4488