Charlotte Payne is looking for love. She's dated lots of men and has been proposed to ten times, but has yet to meet Mr. Right. So Charlotte decides to join a popular online dating site, where she has 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 Leslie, Jill, Mike and Wayne. The test becomes a journey of self-discovery for Charlotte and helps her realize what she truly wants in a relationship.