Most Helpful Guy
You'll have to take some initiative. Give him your phone number if he doesn't have it already and ask him, "Now you will call me up and ask me out, won't you?" Then give him a big smile.
Most Helpful Girl
It seems like you've been seeing him casually for a while and you want more now. If that's the case, just be honest with him. There is no room for the misinterpretations of hints when it comes to your feelings.
The next time you *see* him let him know that you've enjoyed the time you've spent together and that you like him, but would like for him to consider dating you in the traditional sense. It can be nerve-wrecking to do, but in the long run, you won't invest time and your heart into someone who isn't looking for the same thing as you.