Kaity Kinney and Matt Dwyer meet when they are in their teens while working after-school jobs at the same Chicago grocery store. The two become good friends but go down different paths in life and lose touch. Matt contacts Kaity nearly twenty-five years later, and they catch up with one another's lives, reminiscing about the shared events of their youth and remembering the people they both knew. As their friendship blooms, their relationship becomes more intense. Determined to find out if Matt might be the man of her dreams, Kaity accepts Matt's invitation to reconnect in person so that they can have a serious conversation about life and love. And Kaity wonders, could Matt be "The One?"