new here/need guys opinions

I am just curious how some of you let a girl know you like them. I am in a situation right now where the guy and I are great friends and like each other quite a bit. He has asked me if I want to be roommates with him next year when his lease is up and I was wondering if a guy would ask a girl to do that even if they did not like them more than friends. He does things like embarrassing me in front of people just by acting stupid or saying things like "she touched me" in a room full of strangers (yes very immature but I think it is cute). Lately he is always making sure to tell me about all of the girls he thinks is cute and how he went to the gym and saw cute girls and then he will say oh there was guy there you would like. When we drive somewhere he slows down to look at other girls but speeds up past the guys so I can not get a good look in. I even noticed him watching guys look at me then he glances to see if I am looking or atleas it seems that is what is happening. He always wants to go do stuff together (witch is fine with me). But here is the confusing part for me. He has been talking to a friend (girl) online for almost a year. She is very pretty and seems very nice. He tells me sometimes he wants to go to Thailand to see her and if it works out he wants to bring her back with him. Now she does not want to live here nor he there so I am like ok why bother. Then he will ask me "will you go with me to Thailand?". I tell him nothat is just wierd why would I want to be a third wheel. The odd thing is that he had a chance to go there to meet her but did not instead he bought a car and got an apartment. So I am thinking if he wanted to go he would have. Maybe he is trying to make me jealous? He never used to talk about other girls this much it is like he is trying to get a reaction from me but I play it cool and am like stone lmao. We do spend a lot of time talking about everything, he has a son that he never gets to see and sometimes he crys about it and I want to hug him but dont kow if that would be okay I am trying to figure out our boundaries. I do feel a very strong connection between us. I think I know more about him than anyone. So sometimes I feel this is going somewhere then he throws a curve ball at me and says stuff like "why don't you have any cute friends?" and then turns around and says "I am too scared to ask girls out". So what does this mean. Yes to some it seems obvious that he likes me but I have been asking only girls so it is one sided. Is it possible that he just thinks of me as a good friend? That would be ok as well. What are some ways to find out how he feels with out wrecking the relationship? Basically I do not want to ask him if he likes me. I have been trying to make him jealous to see his reaction but he ignores what I say or seems uninterested so I need help. Thank you