Dear Yenta,

How can I tell if my next meeting is a date?  We got drinks to talk business and then we got dinner again to talk business.  And then, we got dinner again to talk business and I paid.  Then in an e-mail we talked a little business, she said, “Going out of town, when I get back, let’s hang out.”  Which is different from business, but our business is kindof a business of hanging out. Is it, or is it not, a date?

-Cornelius

Whatever you do, try not to be creepy/skeazy or sleazy. Photo courtesy of Victor Jeffreys II, phiary.com/diary/victor.

Dear Confused Cornelius,

A few things…

1) It is not a formal date. A date is obvious, and not veiled in business.  A better question, Is it romantic?  This only you and this woman know, and to test these waters all you need to do is dip a toe in and check the temperature.  If it is freezing, retreat and continue business chatter, if it is warm, proceed.  You know this.

2) When you paid for a meal you tilted the power dynamic which is often, oddly, a tilt towards romance.  Whenever it is not split evenly, you are making a statement about something, somehow.

3) Don’t mix business with pleasure.  This is simple and sane wisdom of the sages and is a good rule of thumb to follow…depending on the type of business.  If advancing sexually towards this person could potentially complicate your job and threaten your professional relationship, then heel, boy, heel.  If your business is one that can handle a bending of boundaries, OR, if you really think this is for real, then proceed.

The semantics of dating are irrelevant.  All that matters is whether you really want this person, and if so, then fearlessly pursue them and deal with the consequences, for good or for evil.

Or, when it doubt, said a rogue therapist of mine, do without.

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