When widower Frank finds a picture of his first love, Claire, his young friend Megan, proprietor of the cafe he frequents, convinces him to go on a road trip to track her down. Though reluctant, Frank agrees to the trip when he sees that it might help Megan recover from her recently broken engagement. The two set off on their adventure and find themselves opening up to each other. Along the way, Megan has an awkward run-in with a man and his dog that she can't seem to shake off. The pair soon arrive at Claire's address only to find the home vacant. Not deterred from their search, they stay at a nearby lodge where a surreptitious clue ultimately leads the pair to Claire. However, when they don't get the reception they expected, the story of how Frank's first love ended slowly reveals itself. Meanwhile, Megan learns that the man she'd met earlier, Steve, is the lodge's owner. She helps him with some of his holiday responsibilities and they soon warm to each other and find that they are each grappling with their hopes for the future. As Megan helps Frank pursue a second chance at love and he reminds her not to give up on her dreams or her heart, these unlikely friends find that sometimes the closest family is the kind we make.