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 then paired off and the artists painted the portraits of the resident they had picked. 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. Family and friends were invited and made it an 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.