See You in September is an original romantic comedy set in current day Manhattan. The film centers around Lindsay, a beautiful woman who seemingly has it all, but is deeply afraid of commitment. The film begins with Lindsay dumping "Mr. Perfect" when he proposes marriage. Lindsay attempts to figure out with her therapist why she runs away from every good relationship in her life. She seems to be on the verge of a break-through, when she finds out that her therapist takes a vacation for the entire month of August. Shocked that her therapist could do such a thing, she goes on a search for a new therapist and to her horror realizes that she seems to be the only person in Manhattan unaware that all therapists flee NYC for the month of August.
Instead of taking this news lying down, Lindsay enlists the help of her acerbic best friend Monica to come up with a solution. With the assistance of "Craig's List", Lindsay puts together a group therapy session for all Manhattanites who are in need of therapy, but more importantly angry at their therapists for abandoning them.
As the group assembles, we discover a mix of people whose personal problems actually help them to help each other. It is through the group that Lindsay and AJ meet and begin a flirtation, but it is not until Monica and Max (AJ's best friend) challenge Lindsay and AJ to a bet - that they have to date for the month of August and not sleep together - that their real attraction begins. As they get to know each other, they discover that her fear of commitment and his fear of abandonment may be the very things that allow them to trust one another.
Just when it seems that Lindsay may be able to commit to AJ, "Mr. Perfect" shows back up and Lindsay has to decide if she will choose a life that looks perfect on the outside or the messy life with a man who is perfect for her.