If you want to test it, tell him you like to go out drinking too - and, can he recommend any good places?
If he tells you the place they go to, he is less likely to mind you being there and might ask you to join them if you show up. So you go some time when you figure they might be there, and 'accidentally' be where they can say hi to you if they want to.
Personally, that's way more work than I'm willing to go through.
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“For small creatures such as we the vastness is bearable only through love.”
―Carl Sagan