Cute guy [30s/m] moved in across the street and I [29/f] am very socially awkward

So this guy seems a bit introverted and reserved and I am very introverted and very reserved. He is out front all the time working on his car or some carpentry project and I seem to see him everywhere. I even saw him at the Rite Aid down the street. I walked outside and there he was waiting for his friend to come out.

However, I’ve also made extra efforts to be outside and I think by now it’s kinda obvious. I love walking around my neighborhood but I’ve been doing so way, way more. Or finding random excuses to walk outside like taking trash out or getting my mail, whatever. I hoped it was subtle but I don’t think it is.

I’m quite shy so up to this point I’ve said nothing to him and almost never even make eye contact.

Today, I went for my usual morning hike and was walking from my house to the trail. I looked to my left and he was standing there, facing me, and just staring at me. I think by this point he’s curious what my deal is as we see each other everywhere but never speak. This was the first time I had the courage to really look at him and smile. Literally have not been able to do that up to this point.

My friend is friends with his roommate and invited me to an art event he was hosting. So I went. I went so far as to go to an event his roommate was hosting (at a local venue, not their place) as a roundabout way of connecting with him because I’m that. scared. to talk to him. I know, I’m 29. It’s sad. I didn’t actually bring him up to his roommate so I don’t know if he’s single.

I’m definitely shy in general but I think the fact that he lives across the street is why I’ve been extra weird about this. If I do date him and it doesn’t work, living across from each other could be weird.

Does anyone have some advice to help me build up the courage to just talk to this guy? I’ve been crushing on him for two months and I’m just driving myself crazy at this point