How do you get over the idea of being rejected by someone you actually like? (Rejection this time actually seems terrifying)

I (31f) have a crush on a guy (33m) I’ve met at work. Our company is so large that it’s the equivalent of company A doing business with company B for a few months and you meeting that way.

Anyways, I don’t plan to explicitly ask him out (I’m done asking men out…it’s a personal choice with good reasons) but I do want to make it super obvious that I would say yes to a date. I am willing to make it as obvious as possible to where all he has to say is the date and location lol.

The only thing I could think of: We have a shared goal and I was going to say (in a flirty way) “if we hit this goal, you owe me a drink”. When he says “for doing your job” (he teases me for this but fully acknowledges I’m the only one lol), I can say “for being the first one to do her job because I actually care. So that deserves you celebrating with me”. A lot of inside jokes with this one. Not sure if it’s obvious enough. It also shows I do care about the things he cares about.

There are no other options because I suck at this lol.

I’m so nervous to say this because I really like this guy. He’s very reserved but I feel like he’s shown enough mild interest that he might be interested in meeting up outside of work. I’m also in a male dominated field so I do have to be careful about how I come across. We have had private moments where I feel like there is a mutual connection but I’m also not sure (ex maybe he’s just nicer to me because of my role and that’s why he smiles more). Lately, he tends to avoid direct eye contact but I do catch him staring at me (I am the project lead and he’s the equivalent of the client but the looks feel softer…if that makes sense).

I’m so beyond nervous of being rejected and I’m honestly considering chickening out. I know I will hear “you won’t see him again” which is maybe true but that doesn’t seem to make this any better lol. I’ve never cared about asking men out in the past but when I actually like someone, it’s totally different.

Need actual words of encouragement on this. Please don’t try to convince me to just ask him out. This is a hard stance I took after a long time of being the only one to ask men out. It’s not for everyone and I know it’s weird but it’s something I now value.