Charlotte Payne is looking for love and has rejected multiple marriage proposals - but she has yet to meet Mr. Right. When she joins a popular online dating site, she gets a little help from a dating counselor who requires her to take a 100-question compatibility test.
The questions aren't easy for Charlotte to answer, and each one requires her to recount a poignant and humorous time in her life with friends. The test becomes a journey of self-discovery for Charlotte who begins to realize what she truly wants in a relationship.