Well, there's a right point in time. You can start casual. And then you'd need to read the room. You can't propose at the second date. But I'd say if the woman keeps agreeing to spend time with you, you can step it up. Like go to the cinema and watch some tear jerker. Or the new Minions movie, whatever floats your boat. I don't really see the issue here. If you keep enjoying time together, you'll proceed to a point where it's alright to ask what to do with it. Be friends or start a relationship.