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PixelatedTimeMachine, I am not good at the dating, flirting stuff AT ALL so I cannot give you any advice. However, you made me smile the biggest smile when you mentioned how good you felt seeing him after losing 60 pounds! I think it's a situation many of us dream about but don't get to experience. And it's clear that you lost the weight for yourself and not him as you mentioned the crush had fizzled and you had moved on from the job. Congratulations and good luck to you whatever you decided.

You will never know if you don't ask.
Believe it or not guys are just as insecure as we are. Also, maybe he is unsure of the cues also.
My advice is ask him out. If he says no you will have your answer and it will be his loss.
If he says yes give it a shot.
Congrats on the 60 pounds down and more importantly your new found confidence.

I would ASK But have the mindset if he says NO I wont be disappointed because at least I now know you could end up going out and have a great time or not
life should be experienced and enjoyed right

Ideally either ask in person or via a phone call not text or email - but seeing as you don't have his number that makes it a bit more awkward
yes I get not wanting to crash his happy hour but was giving you the time and day he is there a hint - perhaps just happen to go out with some girlfriends at that time and walk past say hi - are you interested in catching up again if so how about we swap numbers so we can arrange a time...
if he seems a bit surprised - say just look for me over there if you do - then go on your way (also give him a chance by maybe having a drink with said friends but do a bar trip on your own so he has a chance to approach you if he wants...

whatever you decide to do hopefully you will be happy