Local boy Ryan Dunne, now a pitcher for Boston College, meets Tenley Parrish, the daughter of a wealthy couple who summer on the Cape. Ryan and Tenley fall in love, much to the chagrin of their families, while Ryan clings to one last hope of being discovered and signed to a pro baseball contract.

Will Truman and Grace Adler are best friends living in New York, and when Grace's engagement falls apart, she moves in with Will. Together, along with their friends, they go through the trials of dating, sex, relationships and their careers, butting heads at times but ultimately supporting one another while exchanging plenty of witty banter along the way.