Give up and never know? Or try and potentially get really hurt?

I realize that this will be very long, but I kind of desperately need some help. I don't think I've faced such a conflicting concern ever before in my life.

Anyway, I've never been much of the "real life" relationship type of stuff, though I am 22 and have only ever been in one relationship that lasted two years and a majority of it was long distance. Anyway, when I was 18, I started dating this boy and during the midst of our relationship, I formed a strong friendship with another boy who was 16. I have never had such a friendship before in my entire life. I literally told him almost everything, and opened up to him in ways I had never done before with anyone else. He did the same with me. This entire time (for about 10 months) he and I was talk nearly every day. We almost didn't have any secrets at all. After about 5 months into our friendship, he professed his "love" for me. The issue at the time was that I had a boyfriend at the time, and he really wanted me to give up my existing relationship for him. About 10 months into our friendship, he served me with a sort of ultimatum: I either give him up or give up my relationship with my boyfriend.
At the time, I suppose I myself was blinded by love. I was very afraid of giving up my existing relationship. I was young and I believed that giving up my relationship would mean me being lost, having no one, and no where to go. I guess at the time, I just didn't see myself dating my best friend. I knew that I had very small romantic feelings for him at the time of this, but they just were never enough to end my existing relationship where I felt I was in love. So, as a result, he and I stopped talking. It began slowly, and in a few months we basically had little to no contact with each other. He started dating others and I continued on with my existing relationship for another year and a few months afterward. During this time, it seemed to me, clearly, that all the feelings he had once had for me had dissipated and the feelings I had for him and also the desire of a friendship had also dissipated. But despite this, I knew that I had always valued out strong friendship and bond, but felt as if the outcome was really out of my control and there was no help.
So this brings me to today. I have been broken up with the boy that I was dating at the time now for about a year and a half. He and I haven't spoken since. I've tried my way with new relationships (romantic and friendships) but I have had no luck. I haven't been able to start anything romantic with anyone simply because I just feel like being in a relationship right now isn't right for me. I haven't been able to form any strong friendships, I'm not sure why this is the case. I guess since he and I ended our best friendship I just haven't had the desire or luck in forming a bond with someone that is remotely as close to what I had with him.
Presently, he just got out of year-long romantic relationship. He and I both began speaking again about a few months ago. It started off with a text maybe once every two weeks, then proceeded to once every week for a while, and now we text periodically each day. This has been going on for about a week now. A few days ago, he and I skyped for an entire night for about 7-8 hours. It was a very strange conversation because out of nowhere, we both started opening up and talking about very personal things as if we never had stopped being friends. Since this time, we skype basically every night and text every now and then within the day. Here is where it starts to be conflicting...
When we talk, I start to get the small romantic feelings that I used to get with him. He talks to me basically the same way he used to, but since then we have both obviously matured a lot. We joke about a lot of things, many romantic things like cuddling, and things such as. But they are only jokes. He always makes jokes such as saying that we are "soul mates" because we are friends again etc. This all just seems strange to me because the way he speaks to me now is the way he spoke to me back four years ago when we were best friends and he was in love with me. While he makes all these romantic jokes, he also playfully says how we also will never date, how he could never kiss me, and things such as to make me believe that there is no romantic tension between us. I find this conflicting because I don't know if there is anything behind the things he says. In my mind, I don't believe that he could possibly still be in love with me or have a thing for me. Though he openly says that I am cute, tells me he misses me throughout the day, and plays other subtle compliments towards me, he also, equivalently, tries to make me believe that there is nothing between us romantically. He is talking to many people right now that he finds attractive, and I, personally, do not believe that I physically compare to any of them. Also not to mention that he has recently (four months ago) gotten out of a year-long relationship with someone he believes and says he was in love with. Thus, it makes sense as to why he is talking to all these attractive other people as a rebound.

Where it gets really troubling is how I feel about all of this. I am not in a relationship. I don't speak to that many people and really don't have any solid friendships. Among all of these factors, in my heart, I feel that I really have a thing for him now. He has been all that I have been thinking about since we have started talking. In my mind, he seems like the perfect person for me being that we have such fond memories, we are alike on many different platforms, and the thought of the small romantic feelings I had for him four years ago are making sense to me and are developing more in a way that I understand them. I really like this kid... but... I don't know what it is that is between us. I don't know what to do.
He asked me to come out to where he lives, which is nine hours away, to visit him for thanksgiving break. I don't even know if he's being serious or not. I know that he wants me to come hang out with him, but I don't know how much he wants to. That's the thing. I don't know how much he wants to be friends with me, and how much of anything in means of any association with me. I don't know what he wants and I was hoping someone could insight me with an idea of what he wants.
Every now and then while I am in class or at work, he would ask me to come home so we could Skype because he misses me. He also randomly says "love you" or "I love you" at night when he is really tired or randomly during the day when he misses me, but when he does these things I feel like he is joking around. The other night he also accidentally called me by his ex's name on Skype. I'm not sure what any of this means because while this may seem flirtatious to me, he still also jokes around a lot with me, jokingly says things trying to push me away and not get too close to him but he does it like in a playful manner. It's like playful harm that he's not trying to inflict but it seems as if he is establishing a strict wall with me or testing to see if I go for some sort of bait like he wants to know what my reaction is to certain things he says. I don't get it.

Does he genuinely want to be my friend? Or is he talking to me now again because he is single, he is hurt, and he has no one else to talk to? Or does he still have feelings for me? Has come across some sort of revelation and seen that the feelings that he thinks he used to have for me really weren't (strong) feelings? Or has he realized that maybe those feelings still exist?