Should I message him???PLZ HELP :(?

This guy I fell in love with and still am moved to Canada a year ago. We never dated but we had that connection. After he moved, we kept in touch though Facebook. He claims he only liked me as a friend and he dated a girl for a week while in Canada so it seems like he's doing perfectly fine while I'm still crying. He calls me sweetheart and tells me he loves talking to me but barely ever starts our convos. So I don't know if he loves me like I love him. Should I keep messaging him or wait till he messages me because I'm scared that might ruin our friendship and just like completely stop us from talking. Also Valentines Day is coming up and I hope he messages me. How do I be flirty without being obvious??? I'm am sooo confused and depressed:( Plz give me advice