Yes but only as a friend...they did meet in filler but not in manga..in the anime filler toshiro seemed worried and was impress with karin's spiritual awareness, he helped her in a football match since karin hurt her leg...they also meet in another filler where toshiro introduced karin to an old woman who took care of him when he came to the world of the living...yuzu and the old woman also made comment on karin being his girlfriend..but no karin is just a friend of his which he some how cares about