From there coversation in episode 13 Hampnie implies he already knows Alice so do you think they went to the same school
Alice is still alive at the end of the anime. I don't know about the other question because I don't think it was ever explained in the anime.
everyone is forgetting that Alice was in the loop 14 years add his age of 16 he is 30 meaning the age difference 2-3 years. plus Alice went travelling and have have met him on his travels.
Alis (not spelled Alice, gosh.) was in a time loop so he's technically as old as Hampnie. It's probable that they crossed paths at one point while he was trying to break the loop.
What do you think?