That's why I say go for it. Get it over with.
There are two possibilities here:
1) He does like you but he is just really shy and socially awkward, in which case if you make the first move, it might be just what he needs to get some confidence and take this thing to the next step.
2) He doesn't like her, for whatever reason, so he'll just say no and she can get on with her life and move on to something else.
If they start striking up a friendship, it's going to make it that much harder when/if he rejects her, so better to do it now.
Don't pussyfoot around.
