Feeling run down by the usual self-improvement programs, a widow (Rachel Dratch) tries going to a dominatrix class.

After a break-up with his long time girlfriend, Charles explores parts of his sexuality that he never allowed himself to explore before.

Sixteen Thousand Dollars imagines a world in which a struggling Black college grad wakes up to find that reparations have finally been paid to descendants of slaves in America. With this new found capital, they must decide how best to spend their reparations, totaling a mere $16,000. Receiving reparations opens up old wounds of slavery, Jim Crow, and systematic oppression.