When high school teacher JOEL RIDGEWAY finally agrees to a blind date his best friend CHARLIE set up, he turns to his drama class students for advice and they offer a few pointers about how to succeed (“Step One, One Step”)

. The date does NOT go well.

But tonight, something pushes Joel out of his comfort zone. After 15 years living as the guy who didn’t get the girl, he gets a love letter from his high school crush, RACHEL MMFORMA (“Misguided”)

, who has since moved to California and gotten her own talk show.  She never responded when Joel confessed his feelings to her in high school, but she hopes it’s not too late. The students tell him to go to California and be with his love, but Joel points out that he is chaperoning their senior trip only days away. His student Nicole tells him that now with social media he can see just what Rachel is up to (“Instawow”). Student ZACH tells Joel about his own search for love (“My Canadian Girlfriend”) that no one believes is real. And Charlie points out that it’s better to leave Rachel in the past. After all, it’s not like Joel can undo 15 years of insecurity. And suddenly Joel realizes that is EXACTLY what he must do.

As he chaperones his students and Charlie on their senior trip, he enlists their help to undo decades of self-doubt by conquering a list of the risks he regrets not taking before he reunites with his love (“I Can’t Adult Today”)

. On his journey he gets help from stranded motorist/ magician, ALI JOURGENSON who joins the bus for a ride to her new gig, while she is dealing with a breakup of her own (“The Amazing Rodrigo”).

When the school bus breaks down in the small town of Leadville, Colorado, it’s a setback but also an opportunity to work on his list, knocking out #16 (Climb A Tree), #11 (Steal Something) and #20 (Make Money As A Street Performer). But as Joel is sitting down for #23 (Get A Tattoo), PRINCIPAL BUTTERMAKER shows up with student NEIL’S two angry dads in tow, and an FBI agent (who turns out to not be an FBI agent, but Rachel’s talent agent and in love with her). The principal wants to know how Joel can be two days behind on a three-day trip, and why parents are under the impression that their kids are headed to L.A instead of the Grand Canyon as planned. He demands that once the bus is repaired, they turn it around and head back home. The kids explain they want to perform on Rachel’s talk show for a chance at fame. But the Principal sings them a lullaby his mother sang to him, about how special he wasn’t (“Special”)

.

Despite the setbacks, Joel has never felt so alive (“Graduation Day”)

. Ali gives Joel her best advice for what to say to Rachel when they reunite, despite Ali’s growing feelings for him (“Nothing But Time”). With his job, his love, and some major prison time at stake, Joel must complete his list, reunite with his crush, and get his students the chance to perform on national television. It’s a musical comedy road trip romance, where they’ll learn the most important lesson about revisiting the past. As Joel says, “We may not be able to go back and change the beginning, but we can start where we are and change how it ends” (“Find Another Way”).