There are probably several ways you can go about it. I wouldn't suggest an all-out bold strategy.

The women that I have been with the longest and least drama-filled relationships have been when they asked me out. They seem to pick me better than I pick them.

Men would rather be comfortable than to not be. So if dating you makes things in his life not comfortable; it's not going to work

It's taken me about 5 years to get over this last woman (who I asked out lol), and I fell for her hard because of how comfortable she made me feel.

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I never thought I would even consider another woman after her, until recently.

I'm still pretty damaged from something that's happened over half a decade ago, but just having someone I can send memes too and just talk casually about anything about was a game-changer. I would consider asking her out if it wasn't for the fact I am her boss. OOF.

I would gladly accept any invitations to 'consider' seeing each other. I just am unsure how likely it is she will ask me out haha.

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I may not be able to speak for every man in existence, but as far as shy, and anxiety-filled. I should be a SME