How often do you bump into each other? If you can rely on there likely being a next encounter, break your approach into smaller goals. Like the other commenter said, start with a “Hi” next time you see them. Then the next time add a little “how are you?” Build upon each interaction. Once you establish the super casual familiarity with each other, you’ll (likely) be more comfortable with expanding the relationship in whatever direction you see fit. Small, achievable wins lead to bigger, more exciting goals!
You’re welcome! And, honestly, having the awareness of possibly bothering him is half the battle of engaging with him without doing so. Trust yourself! Also, in that event, what if he doesn’t feel forced to be nice, but is actually just nice? In my experience, it still feels very flattering despite any awkwardness. The hardest part of things like this is waiting for the opportunity, try not to worry too much about outcomes in the meantime — you got this!