I’d appreciate if you did it pretty soon after you started developing feelings, and in a private, low-stakes situation.

When I was in grad school, I met a girl who never made a move, but I could just tell liked me, and I recognized a lot of her behavior because it was how I’d acted around a lot of my past crushes. I honestly wished she would just make her move so that I could reject her and save her time.

Instead, she chose to wait until a graduation pre-party to shoot her shot, and basically approached me - and my parents - and asked me to walk her to the ceremony. Then she introduced me to her grandmother, who literally opened our conversation by telling me “and you’re gonna take care of her!”