Great Expectations

Posted on | April 23, 2017 | Comments Off

Dear Short Answers:
There is an older divorced woman in town who seems to like my company a lot because she invites me to join her at numerous events (like dinners and parties).  When we go out, she always pays for the meals and the tickets.  I enjoy being with her but there is certainly no “spark” if you know what I mean.  At least not on my side.  I’m concerned that she might be expecting more but I don’t know how to bring it up without insulting her and ruining a very pleasant friendship.  How do I handle this potentially awkward situation?

Dear Randy:
Frankly, Randy, we are more concerned about the financial arrangement. Perhaps if you paid your own way you would worry less.

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