On this week’s episode, Jared and Jordana start out with a pep talk for going back out into the world. Then they answer an email from a listener who doesn’t know if she should ask someone out at their workplace. Is there an appropriate way to show someone you’re interested without making them uncomfortable? A listener gets an unpleasant surprise during the Awkward Sexual Encounter. Later, they weigh in on an email from a listener wondering what it means for her relationship that she actually enjoys dating long distance. Finally, J&J are joined by Wipeout Host Camille Kostek for a round of Red Flag or Deal Breaker that sparks a discussion about skincare, unconventional living situations, and Instagram captions.