After coming to terms with the fact that she must share her work bonus with Greg, Katie encourages him to live a little and the two decide to splurge on an overnight getaway. Meanwhile, Oliver's attempt at a rebellious streak ends in disaster; and after letting Anna-Kat down, Taylor comes to the realization that she needs to step up and be a better big sister.

While Greg enlists Oliver and Anna-Kat's help to drum up new recruits for the Westport Historical Guild, Katie does her best to support Taylor's dreams of becoming the next American Idol.