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Do shy guys appreciate girls making the first move?

I like a guy at work and it's been hard to talk to him because of the usual reasons. He seems to like me too and has been receptive.

However we both seem to stay one step away and not really go past "oh yeah these printers" "hi how are you?"

I'm trying to work on being more assertive. I rehearse asking his help on a project or something random but I chicken out and I haven't been like this in a while. The only guys I asked out were via text and email.

Would he appreciate me being more assertive with trying to develop friendship or even asking him out? Help!
Do shy guys appreciate girls making the first move?
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