In 1960s New York, Walter Stackhouse is a successful architect married to the beautiful Clara who leads a seemingly perfect life. But his fascination with an unsolved murder leads him into a spiral of chaos as he is forced to play cat-and-mouse with a clever killer and an overambitious detective, while at the same time lusting after another woman.
There are many things in life that could do a number on a man's masculinity. Lenny Babbitt has his identity and manhood challenged when his wife Tracy leaves him for a female doctor named Iris who has been treating their autistic son Isaac.
New York City is full of lonely hearts seeking the right match, and what Alice, Robin, Lucy, Meg, Tom and David all have in common is the need to learn how to be single in a world filled with ever-evolving definitions of love.