Hi

Welcome to the game and hope you enjoy it. Im not an expert myself but will try answer to my knowledge.

1. The game decides the teams in the league so there is no way to chose for the two of you to be in the same league. However, if you add each other as friends and have teams of equal or nearly equal quality you stand a greater chance of being put in the same league.

2. You probably are in different servers so try adding him on facebook.

Goodluck in your managerial career.