Jon is well past his glory days on the football field and now coping with life as a single man in his small hometown of Fairhaven, Mass. With the decision to give up his day job on the waterfront, dedicating himself to a full-time writing career, he increasingly seeks honesty and purity in life. Enter Jon's oldest friend Dave (Chris Messina), unexpectedly home for his estranged father's funeral. Impulsive, attractive, and often dangerous, Dave is hell-bent on injecting some spontaneity into his old friends' seemingly banal lives. Jon, Dave, and their divorced friend Sam (Rich Sommer) reacquaint themselves after years filled with life-defining experiences, pushing the limits of their friendship and uncovering secrets from the past.