I am always confused by the “risking of our friendship” part. Are there really people out there who suddenly recoil, scream “EEEEWW!” and then don’t want to be friends anymore? The point being, the only thing you are actually risking is your ego. You are afraid he will reject you romantically and that is scary. But your ego will recover, and you risk missing a great relationship.

I will say this: Go into this with the expectation that it won’t last. At least with this guy. He seems non-committal to say the least. This is not me saying it can’t go extremely well, he can’t get over that phobia of commitment and you guys have a great relationship forever. But I am saying you know how he feels NOW. As long as you understand that he could bolt at any time and you are okay with that and are able to be friends if that is what he decides, then go for it. However, if you are one of those people who tends to get super hurt during a breakup and doesn’t want to see the other person again, you might want to keep it casual.