Restaurant owner Sinclair Penn decides to befriend a homeless young man down on his luck and gives him a second chance at life. He never planned to fall in love with someone so young, but fall he did, and hard, for eighteen-year-old Ian Mills, who reminds Sinclair of himself at that age. Exactly twelve years earlier, wealthy mogul Conrad Banks did the same thing for him and all Conrad ever asked was that he pay it forward.

The world was a cold and dark place, and Ian Mills didn't think he would live to see nineteen at the rate things are going. Not only did his foster parents kick him out of their house with only the clothes on his back, but they cut off all ties with him, leaving him alone and destitute on the streets of Portland. They even took back his cell phone so he had no way to contact anyone for help. When his needed insulin got desperately low, he had no idea where to get a refill.

Then, right before Thanksgiving, an angel of mercy saves him from dying when he passes out in the street after trying to find somewhere to spend the night. When he wakes up safe and sound in a hospital room, Ian promises to repay Sinclair.