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These two characters are first seen together in Monster's Ball. They are seen when Aaron is attempting to leave the dance at the end of it, and Maxfield stops him knowing that Aaron is drunk. Aaron tells him that he sounds like an "uncool dad" before Wes demands his car keys. Aaron sighs and hands them over, asking for some money for a cab home as Wes manages his trust fund.
As he gives him the money, Wes says he saw him talking to Elena Gilbert and warns him away from her. When Aaron asks why, Maxfield replies with because underneath his very uncool exterior, he does care about him. It was revealed that Wes is Aaron's legal guardian and as the younger turns to leave, Wes shouts "be safe" after him.