St. Dunstan’s ‘The Last Five Years’ Proves Love Is All About Timing
Love is complicated. I think we can all agree on that, to some degree. Even good relationships take hard work. Communication is key, and perspective matters, especially in difficult moments. However, perhaps the most heartbreaking part of any relationship is living through the end while remembering the beauty of the beginning. Jason Robert Brown explores that emotional territory in the beautifully tragic The Last Five Years, a musical that takes a traditional love story and tells it in an unconventional way.
At St. Dunstan’s Theatre, this beloved contemporary musical gets an intimate staging, with Andrew Martin and Alyssa Alonte as Jamie Wellerstein and Cathy Hiatt, two people whose love story unfolds in opposite directions. Under the direction of Jamie Richards, the production takes on one of musical theater’s most demanding challenges: telling an emotionally complex story with just two performers, a remarkable score, and a narrative structure that asks audiences to piece together a relationship as it falls apart.
No elaborate ensemble numbers hide behind, and no flashy spectacle distracts from the material’s emotional weight. And perhaps most importantly, there are no easy answers telling you who is right and who is wrong. Instead, The Last Five Years asks audiences to consider something far more interesting: Can two people genuinely love each other and still be completely wrong for one another? It’s a question that doesn’t come with a particularly comforting answer. Then again, the best love stories rarely do.
[Warning: spoilers from St. Dunstan’s Theatre’s production of The Last Five Years are below!]
An out-of-sync love story
Audiences have seen the romance in The Last Five Years play out time and again in so many shows, but what makes this musical so fascinating is its refusal to follow the traditional rules of romantic storytelling. Instead of joining the characters at the beginning of their relationship and moving forward sequentially, we move through time to see both the beginning and the end of their relationship, moving in opposite directions.
When we first meet Jamie, he is an aspiring novelist whose career is just taking off. All the pieces fall into place just as his relationship with Cathy begins to blossom. Meanwhile, Cathy is a struggling actress who can’t seem to catch a break. She loves her husband more than anything and wants to be a supportive wife, but her professional frustrations increasingly bleed into her personal life. At the start, their relationship is all sunshine and rainbows, exactly how it feels to fall for someone. Throughout The Last Five Years, Cathy and Jamie fall in love, get married, and eventually discover that sharing a life doesn’t necessarily mean sharing the same dreams.
On paper, that might sound like a fairly conventional relationship drama. Jason Robert Brown, however, has absolutely no interest in making things that simple, which is where the twist and heartbreak of The Last Five Years truly comes in.
Jamie’s story moves forward chronologically, beginning with the excitement of a new romance and progressing toward the inevitable collapse of his marriage. Cathy’s story, by contrast, runs in reverse, opening with the devastation of their separation before gradually returning to the optimism and innocence of their earliest days together.
The two timelines intersect at their wedding, creating one of the musical’s most meaningful structural moments, and a turning point for both the characters on stage and the audience watching with bated breath. It’s a clever theatrical device, but more importantly, it’s emotionally effective. By letting audiences experience the same relationship from two different directions, Brown shows how perspective can completely reshape our understanding of love.
For Jamie, the relationship begins with possibility and ends in disappointment. For Cathy, it begins in heartbreak and ends with hope. Neither perspective tells the whole story, and that’s precisely the point Jason Robert Brown aimed for. As we’ve said before, relationships are incredibly complicated, and when we see two different perspectives, the audience begins to understand how each person’s view can paint a different picture. There’s a lot of gray area that can be construed differently depending on who’s telling the story, ultimately indicating that neither Jamie nor Cathy is truly the hero or villain.
What makes this unconventional storytelling approach especially devastating is that audiences already know how everything turns out. Every romantic gesture carries an undercurrent of sadness, every hopeful declaration feels just a little more fragile, and every moment of happiness becomes a reminder of what these characters will eventually lose. It’s the theatrical equivalent of looking through an old photo album after a breakup. The smiles are still there, the memories haven’t changed, but everything somehow feels different. We’ve all felt it, adding another layer of depth to an already complex story.
Andrew Martin and Alyssa Alonte expertly walk an emotional tightrope
At the center of St. Dunstan’s production are Andrew Martin and Alyssa Alonte, whose casting brings an especially intriguing dimension to The Last Five Years. The two performers are also a couple offstage, which makes their involvement in a show about a marriage’s unraveling particularly fascinating. Of course, being in a real-life relationship doesn’t automatically translate into convincing theatrical chemistry.
Jamie and Cathy require more than just affection. These characters demand vulnerability, frustration, resentment, humor, and the ability to communicate years of emotional history through relatively brief musical encounters. It’s a demanding assignment for any performers, particularly because The Last Five Years offers very little room for theatrical camouflage.
Andrew Martin’s Jamie can be enormously charming one moment and deeply frustrating the next. His ambition is admirable, his enthusiasm infectious, and his excitement over professional success entirely understandable. Yet those same qualities gradually expose his self-absorption and his inability to see how his achievements affect the person beside him.
The role requires a performer who can embrace Jamie’s charisma without overlooking his flaws. If the character becomes too likable, the relationship’s collapse loses some of its complexity. If he becomes too arrogant, audiences may struggle to understand why Cathy fell in love with him in the first place. Martin finds that balance brilliantly, feeling like the perfect actor to bring this character to life.
From the moment he steps on stage, you can’t help but feel the charm Cathy must have seen from the beginning of their relationship. He’s bursting with enthusiasm, bringing that bubbly personality to the surface and softening the shift you witness about halfway through. It takes incredible talent to bring someone like Jamie to life, and Andrew Martin does it better than anyone.
Alyssa Alonte faces an equally challenging task with Cathy, a character whose emotional journey is arguably even more demanding because it unfolds in reverse. Cathy begins the musical already wounded by the relationship’s failure. As the story moves backward, she gradually sheds that emotional baggage until she reaches the optimism of someone who believes she’s finally found the person she will share her future with.
It’s a fascinating acting challenge because the audience’s understanding of Cathy grows even as the character herself becomes less aware of what’s coming. However, it takes incredible strength to start from anger and work your way back to love. Not many could step into that role and make Cathy feel real. This role demands an actor with fire in her soul, a passion for life, and the ability to be vulnerable in so many ways, which is why Alonte is the perfect Cathy.
From the moment Alonte steps on stage and into “Still Hurting,” her flawless performance gives you chills. She embodies Cathy so perfectly that, at times, it’s hard to tell where the character ends and the actor begins. You feel Cathy’s pain, but more importantly, you see the strength that remains even as her heart breaks. Like Martin, Alyssa Alonte’s performance is so talented that it’s hard to imagine anyone else in the role.
The Last Five Years reminds us why theater matters
Ultimately, the musical’s success depends on whether Jamie and Cathy feel like recognizable human beings rather than convenient representatives of two competing perspectives. They need to be flawed, occasionally selfish, sometimes unreasonable, and still capable of inspiring genuine sympathy. After all, relationships rarely fall apart because one person is entirely good and the other entirely bad. More often, they collapse somewhere in the complicated space between good intentions and poor decisions.
That is exactly what St. Dunstan’s Theatre’s The Last Five Years does perfectly. While Jason Robert Brown’s show has an incredible blueprint, this production succeeds because of its actors. The show isn’t flashy; instead, it uses a simple set, letting the actors shine as they should. It’s a musical that lives and breathes through the talent on stage, making Jamie and Cathy feel fully formed. Andrew Martin and Alyssa Alonte’s vibrant, intoxicating performances elevate this production from great to flawless. St. Dunstan’s Theatre has crafted a professional-level show, thanks largely to the two actors on stage.
The Last Five Years reminds us that relationships are rarely defined by a single moment. They’re built from countless choices, compromises, celebrations, and disappointments, many of which only reveal their significance long after they’ve passed. Sometimes, the person who once represented your entire future eventually becomes part of your past. And sometimes, the most beautiful love stories are the ones that don’t last forever.
That’s the bittersweet brilliance of Jason Robert Brown’s musical, and it’s what makes St. Dunstan’s production such an intriguing exploration of love, loss, and everything that happens in between. When the music finally fades, one thought remains: love may not always last five years, but the memories have a way of lasting much longer.
Check out St. Dunstan’s website for more information about upcoming productions! Did you happen to catch this production of The Last Five Years? What did you think? Share your thoughts on social media and tag @bsb.insider to keep the conversation going!
Exclusive Interview: Andrew Martin and Alyssa Alonte of St. Dunstan’s Theatre’s The Last Five Years
