J&J are ready to dive into another episode, but first, they have a very New Yorker debate and give a preview of the “Win A Date With Jared” submissions. Next, the first emailer has a conundrum. Guys see her as a “cool girl,” which is great, but she’s not too cool for a relationship. How can she overcome that placement in their minds? The Awkward Encounter is what happens when one person tries to force romance. Then, the second emailer is reeling from a breakup while battling a diagnosis. Was her ex wrong for breaking up with her while she’s sick? The episode ends with a round of “Red Flag or Deal Breaker?” about saying “ILY” early on, OnlyFans models, and appearance modifications for men.

Learn more about your ad choices. Visit megaphone.fm/adchoices