In "An Officer and a Gentle Ben," it's Fleet Week and Bonnie is getting ready to meet up with her yearly fling, Captain Hudson. But when the Captain proposes, Bonnie panics and thinks the best way to discourage the Captain is by pretending she's in love with Tucker. Ben and Riley try to define their relationship, but they keep getting their signals crossed. In an effort to move on, Ben and Tucker pose as sailors and manage to get aboard the Navy ship. But when Captain Hudson comes looking for Tucker, their real identities as civilians are quickly exposed. Meanwhile, Riley's co-worker Robyn is impressed with Danny and asks Riley to set them up. But when Robyn and Danny hit it off, will Riley recognize what her best friend really means to her?.