An Aussie Problem

Sage

There's a guy in Australia who I've happened to work and room with off and on for the past year. However he has never told me how he feels about me (he's pretty bad at voicing his feelings), even though we usually talk every day and when we're together we have a lot of fun! At the moment we are miles apart and it's become almost unbearable for me. People say I should get over him but what if he does like me a lot more than he's letting on. Should I tell him how I feel incase I haven't gotten my feelings across to him the past year? If so how the hell do I approach such a thing via messenger...