J&J are diving right in because Dr. Naomi Bernstein, Jordana’s sister and co-host of Oversharing, is in the studio to ease us into this episode. Plus, her husband Jeff tagged along, so we got both sides of their story as they take us back to dating in 2006. Afterwards, Jared sneaks in a mini session about his “hoodfishing” issue on the apps. The first email is from a listener struggling with talking to her boyfriend about grief. She recently lost her dad, but her boyfriend’s obvious discomfort has her holding back, so J&J get some help from Dr. Naomi on how she should proceed. The Awkward Encounter is one single mom’s “what happened in vegas” story. Then, we hear from a listener needing J&J to help her decide whether to give her BF a heads up that her ex will be at a wedding they’re attending soon. Her BF doesn’t want to know about exes, but they’re both in the wedding party, so should an exception be made to avoid an awkward moment? The episode ends with a “Red Flag or Deal Breaker?” about repeating a couples trip to Italy, getting grossed out by period sex, and bizarre eating habits. Learn more about your ad choices. Visit megaphone.fm/adchoices