We're officially headed towards the toughest times to date—cuffing season and the holidays—so Jared and Jordana discuss how to navigate this tricky period. They hear from a patient whose attractive doctor makes her temperature rise but she's unsure whether to make a move or not. Next, they hear an Awkward Encounter about life at boarding school. Then, they discuss an email from a listener whose boyfriend is extremely jealous and suspicious of her male friend. Finally, they dive into a round of "Red Flag or Deal Breaker?" about toilet plungers and gift giving etiquette. Learn more about your ad choices. Visit megaphone.fm/adchoices