I did it but I don't think I would ever do it again because it really didn't pay off.
There was this guy at university whom I had liked very much for quite some time, but he was really shy and reserved so I plucked up all my courage and asked him to go to the movies. I did it all the time, over and and over again, and he always agreed but never initiated any date. We had a great time but it still came to nothing because even after 6 months of this, he still wouldn't go further than a peck on the cheek. I then never contacted him again and he never called me of his own either. Some time later I wrote him a letter asking him what had been wrong, whether he wasn't that into me or whether I had acted weird or anything. His response? He was too shy to try and do anything of his own accord and thought I didn't like him that much ... Huh?? After I had asked him out again and again for half a year?? Men can be so stupid and I have learned my lesson.
So nowadays, iff he doesn't like me enough to ask me out, I will certainly not do it for him, no matter how much I like him.