James (James Gunn), a successful Hollywood screenwriter, and his wife Jenna (Jenna Fischer) decide to celebrate their successes by contributing to a charitable cause. Opting not to help with disease and health efforts, they settle on helping the homeless, though their plan is an unorthodox one. To inspire bums to help themselves and improve their self-esteem, Jenna and James intend to distribute lollipops covered in inspirational wrappers. Jenna taps her wide network of contacts and James toils over inspirational and artistic concepts for the paper wrappers, but their difficulties mount when they struggle to secure corporate sponsorship, assemble a team of volunteers, and actually encounter the people they plan to help.