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Dating Intentionally

282. Flaky Dates, Slow Texters and Catching Feelings When It's Casual (Dating Dilemmas)

July 21 · 25 min · 24.5 MB
0:00-25:33

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Dating today can be a mess, and so much of that mess stems from confusion, uncertainty, and ambiguity showing up in ways that just infuriate us. In this episode, I'm answering four listener dating dilemmas that each capture a different flavor of that chaos, from the planning-phase ghost to the partner whose humor crosses a line to the slow fade that sends you spiraling over someone you barely know. These aren't rare, one-off situations either. I hear versions of these same four patterns constantly, which is exactly why I wanted to break them down together. I'm covering:

  • What to do when a guy keeps initiating dates that never actually happen
  • Why a plan without a set time, date, and location usually isn't a real plan at all
  • How to know if you're being "managerial" by helping plan a date, or just being reasonable
  • How to handle a new boyfriend whose "jokes" cross a real line
  • What it means when a partner says the only way to be with you is to suppress part of himself
  • Whether to say something when a casual connection's slow responses start to bother you
  • How much effort is reasonable to expect when you're not looking for anything serious
  • How to hold onto your sense of self when someone goes quiet after a great phone call
  • How to tell the difference between an old trigger and an actual red flag in the moment


For each one, I give you the exact tweak I'd make if I were in your shoes, along with the bigger pattern underneath so you can spot it before it drains you again. My hope is that you walk away from this episode more decisive, less likely to spiral, and a little more convinced that most of this isn't actually about you.


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