A college counselor watches anxiously as her teenage son applies to college without her help. As her son plans for his future, the counselor and her husband reflect on how quickly their lives have changed, seeking ways to steady themselves in the midst of middle age.

In the year 2000, Orion is a young software developer who’s hit it big with his tech company in Cambridge, Massachusetts. Despite his long-term relationship, success, and newfound riches, he feels an emptiness in his life, leading him into dangerous territory.

An awkward Connecticut professor tries to cure his loneliness by dating tens of women, all to no avail.

A three-years-married couple have lost the spark that once excited them, leading the wife to venture into tentative love affairs.

When a successful economist and a financial consultant in happy marriages engage in an affair, they are forced to navigate through their complex motivations and desires, their incompatibility with each other, and the potential end to their relationship.

A professor in an unhappy marriage obsesses over and fantasizes about a much younger student, imagining how he will age.

A conversation with his former lover opens a man's eyes to his tendency to flee rather than confront the hopeless reality of his own life.

When loving each other becomes inconvenient, a man separates from his wife of 20 years and struggles to realize that the end of marriage must also bring an end to the life they were supposed to live together.

A lonely man in his forties imagines a domestic life with a woman he briefly met who is interested in his furniture, but not his marriage proposal.

When a depressed middle aged man strikes up a romance with his neighbor in a modern suburban American town, he consults women's magazines to make himself into the perfect lover.