Adapted from a recent online discussion.
Question: Getting divorced, and have reconnected with a 20-years-ago lost love. We've hit it off great, and now after two months, she wants to be neither the rebound nor the transitional person. As in, saying to me that I have not healed, I have not experimented, I have not explored my well-deserved freedom.
How do I tell her not a day has gone by in the last 20 years that I have not longed for her? She says, "Go away and tell me when you are ready."
Answer: Go away and come back when you're ready. You may be ready - but since she has decided you aren't, there's no point in arguing. It'll just reinforce her impression that you're not ready. You'll be on stronger footing even if you lie low for a month and return saying, "This is bull, I'm fine."
But: It actually would be worthwhile for you to live completely on your own and develop your own natural rhythms - just to see what they are. Left to your own devices, what do you watch on TV, eat for dinner, fill your free time with, consider your ideal bedtime? Mundane stuff like that.
Knowing these things will help you gauge how much you have to move the needle in a relationship to keep the peace, and that's seriously valuable information. Having a new relationship teed up makes finding your singleton equilibrium all the more important - it's a hedge against romanticizing your one-who-got-away.
Question: A close friend of mine got hard-core dumped by her live-in partner last month. She was upset for about a week, and since then, she's proceeding with an Everything Is Fine, Thanks for Asking policy. She even started dating someone else.
I know everyone processes bad news differently, but I feel totally weird hanging out with her, because the conversation is very light and only occasionally brushes up against the breakup. I'm torn between wanting to ask her how things are going and wanting to let her steer the conversation; I don't want to imply she's doing the breakup "wrong." She values strength, so while she may be doing OK, I suspect it feels good to her to present a strong face to the world, which is a strategy that could backfire.
Answer: If it's an unhealthy choice, then she'll find that out when it backfires.
Ask her how she's doing, but don't make the pity eyebrows when you do; show respect by asking her straight. That will let her know she can trust you not to press, patronize, or judge her if she ever stops being fine. As you almost say yourself, though, this way might actually be better for her because it feels good to her to be strong. See the value in her way, and I bet you'll be that much more of a comfort to her, even if no comforting words are said.