What/If examines the consequences of what happens when acceptable people start doing unacceptable things. Anne is a wily, quick-witted venture capitalist whose success and carefully managed public persona are the result of a torrid devotion to her post-feminist doctrine. Anne makes a lucrative but dubious offer to a couple of young San Francisco couples who are newly married but struggling financially. What if they get an offer too special to refuse? What would you risk for a chance to have it all?