A play written specifically with Valentine's Day in mind, With This Ring is the story of a wedding band that travels over five generations and the visceral effect it has on those couples who come to possess it. The ring is first presented to Irish immigrant Bridget McCoy by her husband Sean at the turn of the nineteenth century. Sean is a police constable in Rockaway Beach, New York. Since he was unable to afford a ring for his bride when they were first married, he worked a second job to make enough money to buy it.

The ring then skips a generation in the 1960s as the couple's grandson Joe McCoy inherits it, has it inscribed, and presents it to his new wife Matty. Joe wants to move from Rockaway Beach to a new house in Long Island, but Matty, an actress/artist, wants to remain in the neighborhood where they both grew up. Joe is worried about the changing demographics of the neighborhood, which proves to be prophetic when he is tragically murdered by a local delivery boy who steals the ring.

In Scene Three, set in the mid-1980s, the ring becomes a point of contention between an estranged couple contemplating a divorce. Paul, a writer who came across the ring in a pawn shop, is living in the sparsely furnished apartment, when his soon to be ex-wife Karen pays him a visit to bring over the divorce papers. During a heated argument over their divorce and the ring, Paul throws the ring out the second story apartment window.

The ring finds its way to Bobby and Liz, an engaged couple in 2007 who is expecting Liz’s Great Aunt Matilda from California for the wedding. It turns out that Bobby found the wedding ring that Paul tossed from the window when he was a kid playing with his toy soldiers outside in the grass. He held on to it and gave it of Liz. Aunt Matilda (Matty McCoy) returns from her exile on the West Coast to discover the ring that was stolen from her and Joe many years before.

Much of the charm of the play is in watching the decades-long transformation of the quaint apartment, part of a Victorian-era mansion in Rockaway Beach, New York, where the author spent his adolescent summer years. Clips of accompanying music from each era plays as the scenes change and add to the flow and mood of the play. The play has received many productions since it was written in 2007.