Grace drags Will along to keep her in check during her first date with Nick only to leave a heated Will at his table for one. Meanwhile, Karen hatches a wild plan to get Jack a date with Aaron, the neighborhood bird enthusiast, only to ruffle some feathers when things don't quite go as planned.

Jack convinces Will that they need a change of scenery and should buy a vacation home in Loudon Falls, 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, Karen befriends Ellen, Grace's (Debra Messing) friend who is having marital problems, and takes her out on the town to drink her problems away.