Samantha Who? Season 2 Episode 9 The Family Vacation ( Air Date 2008-12-01 ) Genre Comedy category. Overview "After the breakup between Owen and Sam, The Newlys, Dena, and Andrea decide to pack it up and head out for an overdue family vacation to a lodge. Sam is met by an unexpected friend at the lodge, Brad, who was her childhood sweetheart. Things get turbulent when Andrea makes a pass at him.".