Be nice. Have friendly conversations. Get to know him.
Trust me.... Ive been constantly pushing and pulling..... for almost over 2 yearsss its really tiring.. don't be like me... always wondering what ifs.
Find something you both have in common and talk to him. I think this will help with making things feel more natural, instead of it being all nerve wracking. Say funny things w/o overdoing it, I think people generally like funny people.