Dear Jewish Fairy Godmother:

Three weeks ago I had a great first date. We talked and laughed and traded
stories. I think this is a guy I could seriously like. But we have made two attempts
to connect since then, and both have ended up with me sitting home wondering
what happened. We are both free-lance consulting, and quickly bonded on the
difficulty of scheduling when we have very little control of our deadlines. Both
times the plans foundered on his end, with less than a few hours notice the first
time, and multiple texts back and forth the second time. In the words of an
economist friend, “The transaction costs seem very high.” I’d like to like him and
don’t want to scare him off, but I feel like a conversation about how we interact is
in order. Is it too early to say, “Here’s what seems reasonable to me if we are
going to get together.”…? Both times I could have done other things and lost the
chance when he bailed on me.

Not A Wallflower

 
Dear Not A Wallflower:

Not at all. It’s not only not too early but very timely. Both of you are
used to selling your time for money, so the value of a missed
opportunity (whether it would have been another date or just
unencumbered time) should be very obvious to him as well as you. It’s
quite reasonable, the next time you actually connect (in person best),
to start a conversation that goes roughly like this: I’m happy to be
flexible when we connect, as long as it is mutual and reciprocal. I
respect deadlines, but not whims. If we have actual tickets or specific
plans, I need enough notice to find an alternative date. But if we’re
just meeting for coffee or a meal, I am usually accommodating. If it’s
habitual it will not help this friendship. But if it’s urgent, I get it.
BTW, I wouldn’t lead with that, lest it taint the date. But I would be
clear when you say it. With a smile.