Missing Friend

Logged into League a few days ago with some friends, but one of them wasn't on my friends list entirely (in Offline or General). We joined on someone else, but still couldn't friend each other from the lobby. Typing in the friend request through the search feature says that the request goes through, but he isn't added to the 'Sent Friend Requests' group there. Aside from not being able to be friends, we can't read each other's lobby or in-game text. As far as I know, this only happened with him on my end and me on his end. Anyone else ever experienced a similar issue or know a possible workaround?