Alan starts dating two women at the same time, and things initially work out without a hitch. Alan dismisses Charlie's advice that things could get complicated, and that he should have lies ready just in case they start to suspect he's two timing them. Naturally, Alan is put in the hot seat when he is asked directly by one of the women if he is seeing other people. He stammers for a moment and admits that yes, he is, and she kicks him out. After getting the boot from his first girlfriend, he heads over to the second's house to surprise her. Once there he discovers that she too is seeing other people, and he ends up losing both of his girlfriends in the same night. Meanwhile, Jake has his first experience with alcohol, and Charlie is forced to help him deal with the effects of drinking too much.
