Helping someone in any deep sense requires immensely sensitive understanding. This is especially so because the one seeking help is very often engaged in tacit acts of resistance.
In other words, he doesn’t know that he’s fighting what is being offered or, more generally, that he’s fighting you. His mind, yes, is his biggest enemy, and yet it’s also something that you, the one possibly seeking to offer something to him, need to very keenly understand.
And you need to keenly understand his mind because it’s the only way to slip something edifying past his defenses–if you do slip something past. When in doubt about extending the hand, know that very often less is more and that silence is not nothing. The Daoist view of non-intervention is a safe bet.
Know that this person is on her own spiritual journey and that it’s often wise to say little or, in any case, to say less. Circumspection is a gift, one that will virtually never receive a remark yet may leave a faint, faintly loving mark.