How Can I break the social norm by making a first move?

I have a job offer and will be resigning from my current position in two weeks.

My coworker crush and I work on the same very large floor in different offices. We met in Decemeber during the company holiday party and we had a nice chat about our positions and education. The conversation was very causal and it felt very comfortable taking to him. After we spoke, while mingling with other people I caught him giving me the eye.

To be honest, ever since that encounter I have been intimidated by him. He is very good looking, has a higher rank in the company, and is about 10 years my senior. I saw him on another occasion and was like a deer in headlights.I think he might have sensed that and maybe took it for stand offishness.

We see each other every now and then but all he says is hi and keeps it moving.

I just wanted to know if I should make a move and how. It would not be the end of my world if I didn't/ was rejected. I'm just trying to be a little more outgoing in life I general and don't want to have any what ifs when I leave.

Your thoughts?