Thank you so much for your advice! Your comment reminded me of a rather key moment that happened:

He and his friend picked a guy to matchmake me with, I said he’s not my type, to which my crush asked “who is your type?” but I didn’t get a chance to respond because his friend interrupted. Right after that, he called me bro again, and I asked him straight up “Do you see me as a bro?” He clammed up and seemed like he wanted to say something more, but just said “What?” while smiling after a silence, and I said “What?” back. At one point, we were almost cuddling and his voice got cute/soft; he also initiated a hug late that night.

I like the idea of asking our mutual friend to help me out and ask him directly if he’s interested in me that way. I’ve already chatted with his friend, hinting at my feelings, but I haven’t asked him to open the dialogue on their side. His friend seems very supportive and said that we would be a cute couple together. For additional context, he also did mention that the earliest he will start dating is after this strenuous work period which goes until mid-December. Given the timeline, do you think this should be as soon as the work wraps up right before the holidays, or wait until next year? Not sure if I can keep waiting in frustration especially wanting to make the most of the time off.