There a thousands of similar questions on Yahoo answers (all from girls). You should check them out sometime.
I'll give you the same answer I give all of those thousands- approach him about going out on a date (don't say the d word to him though)- ask him if he wants to see a film, go for coffee, whatever you prefer. If you connect, tell him it would be nice to do it again sometime and build on it.
ChihuahuaMomma basically summed this up. What would be considered role reversal in the mid 20th century is okay now. Just don't be shy with him.
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