Well, I tend not to play conversation games with someone I'm interested in. I flirt, then I ask them if they want to go out on a date sometime. I'm very direct.
If he's interested, he will talk to you in person and ask you those questions in person and probably initiate a date with you in person, via text, or via phone.
So, you're saying it's LD? LD's don't work! Been there, done that, got the jacket for the club membership. If it's long distance, DON'T DO IT! If it's short distance, go for it!
I will do my best to reply with an educated, humble and honest answer. Ultimately, it is up to you whether you want to listen to my advice or ignore it completely. Sometimes, my advice may be wrong; occasionally, it will be right. Regardless, I want to do my best to give people answers they are seeking.