If he turned in his tome of discord, you can't buff or heal him. Otherwise, there shouldn't be anything stopping you. Its possible that he had a higher level buff on, so your buff didn't stack. That could make it seem like the heals aren't doing anything too. A 5 hp heal isn't going to make any noticable difference if he has a ton of hp from buffs.
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Uuur - Your favorite Master +1 cleric <LifeAlert>
Rockwell - Your favorite 30 virgin <Aspen and Rockwell>
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