it means that he cares about you but is too manly to tell you but he will in due time.
Sure. How else will she know? I suppose you could pull a Cyrano de Bergerac, but eventually she'll need to know it's you.
It is that important that you blurt out you really like her. Just muster up all you have and go ask her out on a date. Take it slow and remember, everyone that goes out on that first date (even those so-called confident people) get butterflies in their stomaches and are nervous. Don't try to hard, just be attentive, have fun and don't worry about it.
maybe he is the one that is seeing or sleeping with someone else. I think you should be asking him those same questions.