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.

When Grace convinces Karen to accompany her to her father Martin's birthday bash, the situation turns awkward when it is just the three of them. Struggling to gain the attention of her seemingly aloof father, Grace tags along with him to the golf range in hopes of scoring some quality bonding time. Meanwhile, Karen keeps herself entertained with Martin's buddy, Burt Wolfe. Excited about the date that Jack has arranged for him, Will discovers the true meaning of the phrase "blind date.".