You ever hear those stories about high school sweet hearts who go on to get married and live happily ever after? This isn't one of those. An overweight, theater loving outcast and a teen mom. An unlikely duo...yet somehow they became best friends. After graduating high school they lost touch and that's where their story ends. Right? Maybe not. Pediatric cardiologist, Indigo Stone is over relationships. His search for a real connection keeps coming up short and he's way too busy finishing his fellowship to date anyway. Single mom and caterer Rikki Hendrix quit love. After a string of bad relationships she decided enough was enough. Her son is her one and only priority. A chance run in throws a wrench into both their plans. As an old friendship is rekindled it's clear that things have changed. While they explore this new dynamic of their relationship its hard not to wonder if that improbable high school friendship was the start to their happily ever after all along.