“The timing has always been bad until now. What do I do?”

Q—I’ve had an off-and-on-again dating experience with someone I now really like. It seems that the timing for both of us has just been bad until now. We recently had a great date and then kind of an awkward date. Do I just wait for him to make the next move?   I’m hoping he asks me out this week or next, but if he doesn’t, what can I do?  I want to communicate to him that I’m interested and available and that the timing is good.  I don’t want to wonder what could have been with someone where things could have been great. I’m ready to risk but don’t want to turn him off in doing so.

A—I always recommend “If in doubt, spell it out.” Just don’t do it in a way that adds pressure. Give him a chance to show what he would do on his own (a few weeks or so). If nothing changes in his investment after a few weeks, simply say the next time you see him, “Just so you know, I’m at a good place in my life right now and would love to spend more time with you. Let me know if you would like to do the same. I think your are great.” Then smile warmly, give him a big hug, and walk confidently away.

This will relieve you of the worry that there might be some misunderstanding. I hope this helps.

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