One December afternoon a group of artists walked into a local nursing home and drew the names of it's residents out of a hat. They artists paired off with the residents they chose and painted their portraits. During which, filmmaker Jeffrey Vincent Parise went around and asked the residents questions about life, love and art. Three weeks later, there was a group art show at the home, displaying all of the finished portraits. Portions of the proceeds were donated to The Alzheimer's Association. Family and friends were invited to make it a fun and extraordinary evening. In this touching and often times hilarious documentary we see a generational bridge crossed by two unlikely groups. Both the residents and the artists have an experience that was perhaps more than they had bargained for.