Peter and Lois's marriage hits a bit of a snag. When Brian wins the New England Rising Writer's award, the three of them head to Martha's Vineyard for a nice relaxing vacation. Peter's usual drinking habits take over, and he soon spirals out of control, as does Brian's self restraint, as he soon professes his love for Lois. Peter and Brian test their friendship over the woman of their dreams.
Bart teams up with a new kid at school, Donny, to pull some pranks, but when the hijinks go haywire, Groundskeeper Willie tips Bart off to the fact that there might be a rat amongst his friends. Meanwhile, Homer becomes attached to a loaner vehicle while his is in the shop being repaired.