If you send hints like "someone wants to #reunite" I'm sure the recipient will accept just to find out who the person is regardless of what their offline intentions are. Since your identity is revealed anyway I don't see how this saves you from the perceived embarrassment of just asking the person directly.
In the past I've often desired and tried asking for things subtly or in a round about way so as to hunt at what I want without the risk if rejection. In my experience it's not a great path to take.
If the fear of rejection outweighs the potential benefits and you can't bring yourself to ask (for a date, raise, reunion, etc.) then maybe you just don't want as much as you think you do.
When you want something deeply enough you'll ask for it without fear or embarrassment.