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age
41-50,
anonymous
writes: I have a crush on my daughter’s teacher, I have posted a question before asking how I would get him to ask me out, but with several attempts I have noticed it is going to be a lot harder because he has all the traits of a VERY shy guy. He acts like he is interested in me but when I get near him; he gets really nervous and runs in the other direction. So I was wondering what you would think of this idea in my attempts to ask him out. I would like to ask a friend of mine (who he doesn’t know) to tell him that someone is interested in getting to know him but is having trouble trying to get the right opportunity in doing so, what do you suggest she does? (Via a Facebook message), and find out what his response would be and then act on it? That way it would encourage communication outside of the school environment. What do you guys think?
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reader, anonymous, writes (16 March 2013): This is verified as being by the original poster of the questionThank you for your advise, I approached him this week and asked him about a sport that I know that he teachers, I didn’t flirt as I just wanted to break the ice, I was so wrapped up in my own nerves that I don’t recall much about what he said, but I like him even more as he was well mannered and grateful that I asked, I don’t know how I can follow this up.
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female
reader, chigirl  +, writes (9 March 2013):
 I rather think you ought to be direct and just ask him. My experience with shy guys is that they are also hopelessly clueless, and can't take a hint. You got to be direct, or else they wont understand what you're aiming at.
Just tell him you think he's nice, and would like to get to know him better. Ask if maybe he wants to have a cup of coffee with you one day. If he says yes, then set the date right then and there, by suggesting a time and a place. Alternatively, ask for his number so you can text/call him and agree on where to meet up later on.
And if he says no.. Then no harm done. It's a free country, you're free to ask, he's free to say no, and there's no need to feel embarrassed. Maybe he has a girlfriend already, or maybe he's smitten with someone else, him saying no isn't a rejection of you as a person. Remember that.
Just ask him out.
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