Being a waitress at thirty was never part of Annie Ferguson's plan. Neither was feeling trapped in a relationship with a man she wasn't sure she was in love with anymore. As she examines her life she finds she's heading down a path she doesn't want to travel and must correct it before it's too late.

The spark has disappeared in Annie and Andre's relationship, and she knows she can either attempt to rekindle the fire or reluctantly accept that the relationship has run its course. During this trying period in her life, Annie befriends Jon, an unemployed Boston transplant who lives across the hall, and Bill, a kind, reclusive older gentleman who frequents the diner where Annie works. Widowed with children who refuse to speak to him, Bill sees Annie as the daughter he could have a relationship with and challenges her to find her true self and rediscover her dreams.

As Annie, Jon and Bill deal with their own internal struggles they form an unexpected bond; one that is threatened to be broken up by distance if they each follow the path that would truly make them happy.