why not?
If you really want to date him, I say ask him out.
I'm 42 and have asked men out. I think of it this way:
Right now I have nothing. No date.
I ask the guy out. I either have a date or no date.
Like Jiri wrote, "Upside huge"
Most men are flattered.
When it comes to the fact that you might do business with him...that's currently unknown. A male friend once told me when I went into what I think of as "female mode" thinking of all the nuances, he advised, "Go with what you know now." He also said, "Men never think of all the stuff women think about."
It also comes down to how comfortable you are with asking him out. If it's a big deal in your mind, you might be indicating this to him in some way which might make him uncomfortable.
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