Ruthie is on cloud nine when an emotional Eric and Annie reluctantly agree to let her go on her first official date. However, Ruthie isn't surprised to find the family handling her big news with their usual crazy Camden ways: Annie and Lucy decide it's their job to help Ruthie prepare for her date with Vincent (guest star Thomas Dekker); Kevin takes it upon himself to give Ruthie "the talk"; Sam and David change into their Sunday best so they can go on the date as well; an overprotective Martin and Mac (guest star Kyle Searles) decide to spy on Ruthie and Vincent's date; and Matt volunteers to play chaperone, but finds himself in a web of lies to protect Ruthie's feelings.