Jill meets a woman who eloped on her first date and a man who hasn't had sex in decades! She gives a young couple advice on how to enjoy different kinds of sex, and uses a mirroring technique to help a mom and son improve their communication.

A couple looking for a house get more than they bargained for when Jill goes undercover as a real estate agent. Plus, a girl with a boyfriend she's never even seen, a girl who gets kinky in costumes, and a virgin afraid of her own sexuality.