How do I engage with a shy guy when I'm a bit shy myself?

Met a guy at work (hes a customer of mine), we say hi and stuff like that, but if i try much more its a bit awkward. We're both a bit shy. I have seen him check me out on a number of occasions and the way he smiles at me is adorable, but when it comes to talking its a bit flat lol.
Im new to entering the dating game after a long time, he's single too by the way.

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  • An idea that I got from Ben Franklin's autobiography:

    Ask him to do you a favor. For example, tell him there is a speaker that will give a presentation at a local school (or library), and you really would like to attend, but you get panicky about going into an auditorium... alone in a room full of strangers. And if he has any interest, and it wouldn't be inconvenient, etc.

    Maybe that's a bit much. A different example: Ask him to read a sales presentation (or brochure) that you have written and give you feed back about whether it's good or still needs improvement.

    People get a warm & fuzzy feeling when they can help someone else. And when he obliges your request, then you thank him. Very sincerely. And offer to buy him a drink... coffee or beer, whatever.

    Good luck.

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