[client] Cant friend a level 5 new user

I recently introduced a friend to League and he began playing his acct on my computer because league wouldnt load on his. he tried to friend me and it said a request had been sent. i log on to my acct later and there was no req. he eventually manages to load League on his comp and we are both logged in smultaneously and so i sent him a req and he didnt see it. he joined a custom game of mine and the add friend button was grayed out and unclickable. his summoner name is Pete58 and his acct is Pete5811.