Jordana and Jared start the show with a conversation about Halloween and dating. A listener writes in to ask if her boyfriend secretly has a crush on his roommate, and whether or not it’s weird that he and the roommate are doing a couples costume for Halloween. This week’s Awkward Sexual Encounter involves a Halloween costume, a circus theme, and some spontaneous role play. Then another emailer asks if she should hold off on dating again after a difficult breakup. At what point do you admit that you might never get closure and start dating again? Finally, they close things out with some Red Flag or Deal Breakers, including one about using coupons on a first date.