On this week’s episode, Jared and Jordana start out with a recap of Jared’s time at a chili cookoff and the correct pronunciation of Nevada. The first emailer writes in after a guy she went on five dates with seemed spooked after she pointed out that it was, in fact, their fifth date. Are fifth dates really that big of a deal? The Awkward Sexual Encounter involves a missing pair of underwear. Later, a listener asks if she should give her boyfriend a vacation hall pass. Will they regret not having more sexual experiences before they settle down? Finally, J&J play a round of Red Flag or Deal Breaker about ball scratching, happy hour, and elaborate jokes. Learn more about your ad choices. Visit megaphone.fm/adchoices