Dylan has just received a one-two punch that has caused his entire world to fall down around him. One, he finds out that he is being let go at work and that he has to train his replacement. Two, he finds out that he will shortly be losing the room he has been renting. As Dylan desperately tries and fails to find a new job and home, he begins to train his replacement, very reluctantly. However, as he trains Ruby – a sweet, bubbly girl from South Carolina – he begins to fall for her and her rare optimism. But as Dylan works to rebuild his ruined self into the image of Ruby's perfect man – one who is strong and independent – he does so unaware as to why Ruby values independence over everything else.