Excellent and thoughtful replies, thanks everyone.
I think the fundamental issue my friend and I have is that we see the world in different ways. Me increasingly through the lens of dhamma and the 4 noble truths, and he through the lens of a regular joe trying to make his way in the world. He does do a lot of good in his community, he's a primary-school teacher, but his whole world is about finding the perfect woman and a good job, and having a laugh with his mates over a beer.
He's a very open-minded chap though, and I enjoy his company. I'm sure he and I will talk on this point again (not to mention what my parents and brothers will say when I ordain), so I thank you all for your perspectives and suggestions.