What should Too Shy-y-y do?
Ask him on a date, and be very clear that it's a date. Maybe even, "Would you like to go on a date with me sometime?"
Don't complicate things with a Big Talk yet -- just casually ask him out for a drink next time he stops by your desk to say goodbye, and then play things by ear.
Shy guys scare easily. Be friendly and flirty and encouraging and bide your time; things will progress soon enough.
It's been months since you got topless and you still don't know?! Sounds like a dead-end to me -- move on!
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