Wes invites his best friend Chris over for a night in after being dumped by Henry. They attempt to blow off some steam by prank calling strangers, but soon realize that may have been the worst idea ever.

After moving to Chicago for art school, Sam (Nathan Adloff) begins turning tricks to help pay the bills. His longtime, long-distance boyfriend Aaron (Taylor Reed) can't stand to be apart and joins him, determined to find enough work so that Sam can give up having sex for money. When the two decide to tie the knot and move to a state where they can marry, their financial worries intensify... until Aaron spies on Sam with a prominent client (played by acclaimed indie filmmaker Joe Swanberg), and everything takes a wicked turn.