When Carrie starts dating Bill, an investment counselor from Boston whom she met at an art gallery, she tries to include him in her circle of friends, but things become strained as her old friends realize that they can never be part of Bill's world. Kurt revives an old habit pattern by running out an getting a new girlfriend when he learns that Carrie is dating someone new. Shannon is besieged by the men of Gloucester calling her for dates now that she's ended her relationship with Scott. And when Carrie cancels her weekend camping trip with her friends to go to St. Bart's with Bill, Denise is openly envious, but Bill can't put aside his workaholic habits long enough to have any fun, and Carrie wishes she were back home hanging out with her friends instead.