DO NOT do this to "nudge his confidence" or as a "favor" to him. If you like him, then pursue him. If you feel sorry for him, be his friend. If this becomes You giving a service to Him, your relationship will be all screwed up.
Having a girl who likes him enough to talk with him and pay attention to him and maybe even, just maybe, really have deeper feelings for him will raise his spirits. Having a girl take pity on him will CRUSH him in the end. It will prove to him that he really is inferior, even if you think he isn't!