Okay, but it’s not that weird if someone turns you down politely. It’s not that weird. You’ll see him at birthday parties (maybe) twice a year and maybe make awkward chit chat if he’s not into it?
I am not a man, but essentially, yes I was bold with my husband, twelvish or more years ago. I can be pretty shy, but I go after the guys I like.
Ask him for a drink to talk about insurance, now that you are single. He’ll follow up or he won’t. That’s not bold and sends a point. If he takes you for a drink, you can then tell him you need to be clear, you’re interested in him and maybe tell him what you want if he’s interested. If he’s not interested, says thanks, pay for your drink and your tip and leave. It’s not that awkward.