The "Sound of Music Sing-Along" has come to town and no one is more excited than Grace. She plans for her and Will to attend the musical in character-like style by dressing up in costumes. However, her presumed-to-be fun night turns into a disaster when she ends up babysitting a group of children and Will accidentally goes to the wrong theater becoming further detained by James (guest star Taye Diggs), a handsome man he meets. Meanwhile, Karen (Megan Mullally) and Jack (Sean Hayes) try to flee when she gets in trouble with the theater's manager, who blocks off the exits, trapping everyone inside and forcing them to plot their escape. Shelley Morrison also stars.