Dear J & J: I met this woman and we seemed to hit it off, but every time I call to ask her out, I seem to get a voice mail. There’s a part of me that just wants to ask her out on the message. On a scale of one to ten, how bad would that really be?
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JILL: One question: has she ever called you back? If not, this should give you an indication of what her answer might be.
JACK: As a general rule, I don’t like leaving invites on a machine — and particularly when you can’t seem to get in touch with the woman. I assume she owns a phone; has she called you back? How long does it generally take her to return your calls? Has she left vague messages, or messages that indicate when she’ll be available to talk? A failure to make an effort to end the phone tag is a clear indication that you should refrain from further extending yourself by leaving an invite on the machine. If she has taken some of the positive steps described above, follow through by calling when indicated and ask her out in real-time.