Should I Track Down The Guy Who Didn’t Take My Number?

I sat next to an attractive man last night at a political function that included a formal, sit-down, 14-course dinner. This man and I chatted during the time he was there. Another attendee asked for my business card (because of a mutual acquaintance.) At the same time, the attractive man had to sneak out early, and said his goodbyes to the table. He hesitated when it came to me, and eyed my business card. I thought about offering him one, but the keynote speaker began a presentation.

Because this man told me where he worked (I am familiar with the firm,) would it be appropriate for me to send him a short, business-like email saying that I enjoyed talking with him?


In Why He Disappeared, I spent a considerable amount of time distinguishing between the concepts of “right and wrong” and “effective and ineffective.”

As a dating coach, I try my best not to think of things in terms of right and wrong. People have their feelings, their pasts, their impulses and their rationalizations, and it’s certainly not my place to tell them that they are flat-out wrong for feeling what they’re feeling.

Ready for Lasting Love?
Ready for Lasting Love?

However, as a student of human behavior, it’s usually predictable what’s going to happen in a given relationship. From this standpoint, we can more clearly determine what is “effective” when dealing with the opposite sex.

Your dilemma, Robin, is a classic one, since it embodies the whole masculine/feminine energy and societal roles discussion in one simple anecdote.

So instead of answering your question, point-blank, I’d like to ask you: how does dating USUALLY go? If you were to conceive of the most likely scenario about how a couple would go from being strangers to being married, wouldn’t it pan out something like this:

  • Boy meets girl.
  • Boy finds girl attractive and wants to have sex with her.
  • Boy asks girl out for a drink.
  • Girl says yes.
  • Boy calls girl on phone, makes effortless conversation, and comes up with a plan for Saturday night.
  • Boy asks all his friends where to take his gorgeous date and ends up in the same place he takes all of his dates.
  • Girl is surprised that boy does all the right things on the date and is also attracted to him.
  • Boy kisses girl at end of date and promises to call again.
  • Girl kisses him back and agrees to be receptive to further dates.
  • Boy calls the next day.
  • Girl picks up and agrees to go out with him again.
  • 6 weeks later, boy asks girl to be exclusive.
  • Girl says yes.
  • Two and a half years later, boy proposes to girl.
  • Girl says yes.
  • Boy and girl live happily ever after…

Thus, all of those clichés about men liking a chase or a challenge are TRUE.

Notice how it’s always the boy who reaches out and it’s always the girl who says yes. He asks for her number, he chooses a date place, he picks up the check, he tries to kiss her, he offers to call her the next day, he asks for commitment, he proposes.

This is what men have been conditioned to do. I’m not going to speculate whether it’s nature or nurture; I will simply point out that most men have understood this paradigm since third grade.

Thus, all of those clichés about men liking a chase or a challenge are TRUE.

We want to win you over, to earn your love, to conquer you sexually — we don’t want it to be GIVEN to us.

And, to me, that’s the only problem with you stalk—I mean—“looking up” this attractive man at his law firm. Fact is: if he wanted to ask you out, he would have asked you out. How do I know this? Because that’s what men DO.


Sure, there’s always the man who’s impossibly shy and needs someone to give him a pep talk before he can approach a woman. Yet, this is rarely the man women pine over.

Fact is: if he wanted to ask you out, he would have asked you out.

Objectively, it costs you nothing to send him an email and say, “Had a great time meeting you. Wanna grab a drink?” In fact, if it would give you closure, I say go ahead and do it.

I just wouldn’t expect very much in the way of a reply.

He had his chance to ask you out and he opted not to. I would think that would be all the evidence you would need.

Or, as my assistant wrote when forwarding me this question: “If he likes you, he, uh, won’t sneak out of a political function!”