Craig is a struggling family man who loses his low-wage job and is threatened with eviction. In an effort to delay telling his family, he heads to a local bar and encounters an old friend. The two friends are roped into a round of drinks by a charismatic and obscenely wealthy stranger along with his mysterious wife. The couple engages the two friends in a series of innocent dares in exchange for money over the course of the evening, with each challenge upping the ante in both reward and boundaries. It seems like easy and much needed money, but the couple's twisted sense of humor pushes just how far Craig and his friend are willing to go for money and cheap thrills.