How do you put a fresh spin on a stereotypical break-up story? Tell it backwards. And forwards. And then meet in the middle.

That’s the impressive structure of Jason Robert Brown’s The Last 5 Years on now at the Berkeley Street Theatre until May 29.

Cast members Tyley Ross as Jamie and Blythe Wilson as Kathy interact with each other only briefly in the 90-minute, no intermission musical apologue yet the audience gets dragged through half a decade of love and loss in a show jam packed with ebullient wit and audacious songs certain to teach Generation Next a thing or two about transitioning lives and hefty heartache.

The gaping wound is evident in the opening segments of the show when Blythe Wilson’s celestial voice cries out with “Still Hurting.” The mood is set for a roller coaster ride of emotion but, of course, there are always two sides to every story. That’s when Tyley Ross comes in with “Shiksa Goddess,” a joyful number reminiscing the power of love at first sight. The songs are about as sharp in contrast as they come and only here do you realize what kind musical mischief Jason Robert Brown is stirring.

Jamie and Kathy don’t look any different that your average couple that hit it off the moment they meet. But then the confusion sets in during the next step scenario and “Moving Too Fast” rings true of anxiety as Jamie’s indecision gets the best of him. Hold on to your seat as career paths take off in different directions because the sound of worlds crashing down echoes like a loud holler from a mountain side.

But that’s at the end of the story. Or the beginning. Or both. Confused? Don’t be. The Last 5 Years may jump around in time yet there’s still a semi-chronological series of musical events that’ll make you grateful for being a singleton.

Lyrically, Jason Robert Brown nails a handful of extremely comical moments including Kathy’s frustrating summer in Ohio with a midget, stripper, and a snake named Wayne. It’s a song that generate a big applause upon completion. Jamie’s “A Miracle Would Happen” epitomizes the angst over the colloquial ball of chain. Set to an array of songs best described as Beatlesque B-sides, the numbers fit extremely well in succession.

Five years is a hell of a long time for two people to be together. And when it all reaches a dismal end, lives must carry on. For Jamie and Cathy, the lessons learned will last them a lifetime.