Asklemmy

Most people have encouraged you to be direct, and they are right in that it will very quickly get you a yes no answer. And also that it’s more effective on men.

But it’s equally true that if someone isn’t expecting that at all, a confession can surprise and stress them, as they struggle to put their feelings towards you together and decide on a future right in that moment. 

And that can sometimes lead to rejection when it might not have occurred had the way been paved a bit more gradually.

To get specific, that involves doing things with just the two of you. But it also usually involves doing a shared interest, which you’ve said you don’t have.

So if you’re serious, I would suggest you think about what you know of his interests, and seeing if there’s anything you’d potentially like to know more about/get involved in.

Then say something like “hey I’ve started getting into __ a little bit, and I know you’ve been into that for a while, do you know of any __ happening soon I could go to?”

If he has any interest in you at all and is not completely dense, he will usually mention something, and if he does he’ll possibly invite you. Even if it’s like “don’t know of anything now but that sounds fun”, that is also an invitation for you to look up and propose events.

Once you’re at __ together, as the “expert” in the topic he’ll naturally take on more of the “host” role, which will get him talking. If he stops, unfortunately it is usually the woman that has to “go fishing” for topics, since men are not very good at it. Luckily being at __, which you’re not familiar, with means your questions will be real and natural.

And then there is the simple fact that if a man said “I’m cold” and then leaned against a women, he would be thought as creepy, pushy, or presumptuous, but if a woman does it, it’s sweet and endearing even if the man doesn’t like them romantically, because it shows you feel safe with him.

But sometimes, a man doesn’t know how he feels until he’s forced to notice. That will get him to notice. And then he’ll decide, and since men are not very good about hiding their emotions, as they’ve never been forced to, you’ll almost certainly know his decision by how he behaves toward you after that.

And if you think the answers yes, it’s then when you’d be direct. Of course, if you’ve dropped enough hints, maybe you won’t have to.