Chelsea Bledsoe and her husband Graig throw a surprise intervention for her old high school boyfriend, Henry, with a mismatched group of acquaintances from back in the day to fill out the guest list.

Danny and Dolly meet for the first time at a bus stop, both waiting to attend their first day back at high school, but after becoming acquainted, the two decide to ditch school and explore the small town in which Dolly is brand new to, only to end up falling in love with each other after learning of the unusual, not so pretty lives that they both live.