In this unusually lengthy episode, we talk about how to transition from messaging/texting to actual irl dating. We go over the importance of meaningful interactions through messaging, not spending too long in texting limbo (unless you are looking for a pen pal), and coming from a place of self-worth when dealing with occasional rejection. Not-Lilly also shares some specific ways to make someone comfortable enough to ask you out, which led us to discuss the importance of communicating interest.