Thanks again to all who have contributed their suggestions.
In summary of what was suggested:-
1. Be more aggressive
2. Be more touchy-feely
3. Drop more hints
4. Let the alcohol do the talking
And if all of the above fail, flash him my boobs!
I believe I will begin my "mission" soon. Since I don't want to rush things, I will take it slow and easy. Will definitely post an update here should things go my way. Then again, it may take some time before I do.
Thanks also to the dude who upped me. You know who you are.