Jack convinces Will that they need a change of scenery and should buy a vacation home in Middleborough, an up-and-coming gay community. After purchasing a new pad, the duo find out that it is not quite the gay getaway they had imagined. Instead, Jack landed the two in a blue collar town just two hours away from the newest gay hotspot. Meanwhile, Ellen asks Grace to babysit her three children, but changes her mind when she finds out Will is out of town.
The show takes place in New York City and focuses on Will Truman, a gay man and lawyer, and his best friend Grace Adler, a Jewish woman who runs her own interior design firm.
Also featured are their friends Karen Walker, a rich socialite, and Jack McFarland, a struggling actor/singer/dancer who also has had brief careers as an acting teacher, back-up dancer, cater-waiter, talk-show host and student nurse.