I agree, if it a part time job, things are sdimplified for you.If its your regular job do some brainstorming.
Depends on how much you want to take the risk, and I would love to know what your risk assessment came to, because for one you should know that if things don't turn out well in the long run, and you have to see each after that could you be able to handle that.
Just a few points you should put down while thinking of asking him out, are
From your communications with him, what is the most probable answer that he will give.. a yes or no.
If he does give the yes, can you handle the what next...
To play it safe , I think you should consider doing a group office outing, test the waters before you take the deep! And give it time, his mind might be going through the same querries
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