Hmmm, normally I would use the Runes for this question, but I'm getting the feeling the Ogham might be more helpful, so I'll go with that.

I propose asking "What does anonymous most need to understand about his current approach to dating?" with a spread "Setting (context), 'Work' (following through on the plan to use these criteria), and Outcome(s) (what is most likely to happen if you follow this proposed plan).

I'll do your reading today and post when I get the chance to write it up.