Penelope Ward once wrote: “Life is made up of moments that don’t seem important at the time, but they’re what get you to where you are.” Very true. “Now and Then,” another play from Sean Grennan, opens this season at Clare Rose after the playwright closed last season with the highly spoken of “Making God Laugh.” Director James Carey brings a small cast of four together in what he describes as a “fantasy rom-drom.” Even if you guess what’s going on minutes into this production, Grennan’s play keeps you hooked from start to finish, with a script that is as thought-provoking as it is entertaining.

Sharing much of the story while avoiding spoilers is impossible, so we’ll stick to the setup. A Man (Carl DiModugno) walks into a bar in 1982. Bartender Jamie (Mike D’Alto) is closing up as he waits for his girlfriend, Abby (Fianna Rayne Litvok). When Abby arrives, the Man offers to pay for the couple’s time to sit and talk with him. This gesture spins the rest of the play into motion, as stories and experiences are shared among the three while the Man’s hidden agenda slowly comes to light during a game of Truth or Dare. The late arrival of a character merely called The Woman (Amelia Chiaramonte) adds even more layers of complexity and emotion.

As the young couple looks ahead to their future and the older characters contemplate their past, Grennan explores the myriad of decisions that forge the course of a life. Hopes, regrets, dreams, love, loss and that big, inevitable question: What if I went left instead of right?

Carey and this tight-knit cast of sublimely talented actors have created moment after moment, including several masterfully performed monologues. D’Alto’s Jamie knows what he wants, but isn’t sure about what he doesn’t. He brings to life the common dilemma of someone afraid to take the next step forward. As Abby, Litvok seeks a way toward her bigger picture and shows the pain of someone forced to let it go for someone else’s happiness. Chiaramonte, a Clare Rose regular, shows us exactly why she is often utilized in this theater with several commanding bits, including her very memorable and funny one-word entrance near the end of Act I. Finally, the versatile DiModugno returns to the Clare Rose stage in a performance that is funny, yet maddening and heartbreaking at the same time. “Now and Then” is a very thoughtful play you will feel—especially in its final scene, as all four characters realize their happiest moments.

Performance at the Clare Rose Playhouse on the grounds of St. Joseph’s University are on Sept. 29, 30, Oct. 6, 7 at 8 p.m., and Oct. 1 and 8 at 3 p.m. For tickets and information, call the box office at 631-654-0199.