We met on a plane....

I'll try to keep it short mostly because I don't want anyone to stop reading cause its too massive. It spans a 3 yr time period btw.

so there's this guy
and I just can'y figure him out.
I met him on a long trans-atlantic flight. He ended up sitting right next to me on this almost 14 hr flight to Chicago.
We were both 19 at the time and we totally hit it off ! I was so glad to just someone interesting to talk to. We stayed up the whole flight, watching movies and chatting etc..
Of course when the flight landed we parted ways.
But then we remained good friends. He sent me a request on facebook and we used to chat all the time.
Then i suggested we start skyping and we did. He lives in the states and I live in Canada and its kind of ...no ... quite far but he would still say he wanted to visit me.
this did happen....
Last year, over the winter break I flew to the states to visit my aunt and uncle and to stay with them for 2 weeks. I told him about it but he was unfortunately flying out of the country around the time I was there.
By this time, we'd known each other for a good 2 yrs but we were still just friends ... nothing more. Although it would've made me extremely happy caused I had by then developed a massive crush on the guy.

Now... since he away travelling, I didn't really think I could meet him but of course then the Polar Vortex happened.
My return flight got cancelled the last minute. He had texted me saying,"happy journey" etc just before I found out the fate of flight back to Canada. I told him that I'd probably be going the next day.
This coincided with the day he was returning and he said he wanted to come meet me. I was surprised and agreed to meet.
The fellow drove about two hours in that horrid storm and visited me and i just couldn't believe it because this was someone I had known for so little time. some of my much "closer" friends wouldn't do that. Heck even I wouldn't do that for a friend.
Unfortunately he could only stay for an hour and the whole time my aunt and uncle hogged over the conversation :(
Now it's been a year since that happened and we still haven't progressed much.
We chat or skype sometimes and have wonderful conversations but our crazy school schedules don't allow for much free time.
Guys, I've never liked a guy so much.
But i don't know what to do...I'm crazy shy and he's never flirted with me like other guys ( i.e im not sure if he's sending hints or just being nice to me)
I had sworn off obsessing over him a few weeks ago because we hadn't talked to each other for so long but then he wished me for new years and when I said my resolution was to try sleeping early, he said,"ok then ill kiss u goodnight".
Why does he do this !? Im so confused :(
It's usually so easy for me to figure out if a guy likes me but with him its so difficult
Advice from anyone who understands the male psyche.... please, help a girl out

Long distance relationships can be tough. Have you tried telling him how you feel? Or do you act like you're complete friends the entire time?

You've been face to face with this guy for a total of about 15 hours. You don't even know who he is yet you're allowing yourself to believe you have feelings for him. You should just stop responding to his every missive and get yourself rehabbed from him for good. You're stagnating your REAL LIFE DATING CHANCES by not being open in mind/heart(?) to someone who you can actually be with and get to actually KNOW in actions which are what shows you that you can trust to give your love.

He's what we used to call a "Pen Pal" that you happened to have an opportunity to look at face to face for a plane ride and one measly hour in three years.

Break the habit of this so that you can get on with your life. Do NOT tell him how you feel. Unless you're going to be open to moving to where he lives so that you can base your "feelings" on reality telling him you have feelings for him is just folly.