Freed and Issei had a completely antagonistic relationship; Issei hated him. Freed also had a habit of guessing what Issei thinks to the point that Issei almost believed Freed could read his mind. Freed guessed that too.
Even though Asia was allied with Freed at the beginning, he often abused and treated her very poorly. He never cared for her and showed no sadness even when she died.
Though both are swordsmen, they constantly battled between each other and fought as complete polar opposites. He is later defeated by Yuuto Kiba when he achieved his Balance Breaker.
Freed helped Raynare in her scheme to take Asia's twilight healing, but had no real loyalty for her, as he left her to her fate at the hands of Rias Gremory.