J and J start the show with an impromptu conversation about outside pressure to get engaged. Why is the default conversation for so many women to ask each other when the proposal is coming? At 17:20 a listener writes in wondering when it’s okay to ask someone if they’re open to being in a relationship. Is there ever really a good time to ask, or is this the wrong approach altogether? At 40:00 they answer an email from a guy who blew it on the first date and immediately got put in the friend zone. Can you ever recover once you’re put in that category? Another listener asks why she can’t seem to get guys to date her despite being “intimidatingly attractive” and successful. Has anyone ever been too hot to date, or is she just kidding herself? At 1:00:10 they close the show with a round of Red Flag or Deal Breaker. Thanks to our sponsors! Leesa- Order today and get 15% off your purchase for a limited time at leesa.com/UUP and use promo code UUP. Away- For $20 off a suitcase, visit awaytravel.com/UUP and use promo code UUP during checkout!