Jack and Carly are getting tired of exes Stephanie and Sheldon hanging around the apartment so much, so Jack manipulates Stephanie into taking out Sheldon. While out on an errand, Will sees the two in a restaurant sharing a kiss. This news upsets everyone in the family, so Jack tries to undo the relationship, this time with much less success.

Carly's free-spirited, globe-trotting New-Agey friend Rachel Travers is in town. The kids are excited and Jack looks forward to meeting her, but Carly is afraid she might be a mite too free-spirited for Jack. However, Jack insists that Rachel stay with them while she's in town. Jack is a little uncomfortable with Rachel's hugging, vegetarianism and dung-cured Pakistani rugs, but when she counsels Nicole to take some time off before entering college, he can't abide it any longer. Rachel and Jack argue and she storms out of the apartment, leaving Nicole and Carly both upset with Jack.