I was wondering if there is any kind of rule or etiquette about asking out people who frequent your workplace.
Obviously, certain choices are wrong (power issues such as teacher-student), and it's not for when you are dealing directly with the person. I would imagine the last thing most women want is to be asked on a date when all they want to do is order a cup of coffee or have their root canal.
But what about women who frequent where you work and that is the only place you see them? It could make the situation awkward in the future. Not so much for me; asking someone out is just that, and while "yes" would be nice, "no" isn't the end of the world. But the other person may feel strange about returning to your place of business.
Or is this question just much ado about nothing?
Answer: Since about every third letter I get is about how hard it is to meet people, this is clearly ado about something.
And while I'm sure there are myriad rules - say, if you work for a company that doesn't appreciate its amorous employees scaring off the clientele - I think it's something that's otherwise ably governed by a more amusing power: flirtation.
Flirting is the universal, time-proven romantic reconnaissance vehicle. You flirt almost imperceptibly, she flirts back (or not, and you back off); you flirt subtly, she flirts back (or not); you flirt less subtly, she flirts back (or not); you flirt overtly, she flirts back (or not); you realize you've put everyone else off breakfast, you ask her out. Each escalation marks an opportunity for graceful deflection - your cue to back off.
And if she encourages you this far and you still fail and she's not as composed as you are, then, yes, it's unfortunate, but hardly tragic, that she gets her root canals somewhere else. At least, not as tragic as a society in which a guy is so conditioned not to offend that he can't even ask a girl out.