Prayer is hard. We don't the half of us pray half as well as we should like, and we like less than half our praying half as well as God deserves. Different people, however, struggle with prayer in different ways. To some, it's the sheer discipline that's so hard: when in my life can or will I sit down and devote some time to God? For others, it's hard to know what to say besides mentioning the most obvious of burdens and needs. Still others find their prayers cold, feeling as though they are merely talking to themselves or to an empty ceiling. For many of us, it's a combination of these problems, and even more.

It is the last of these which I've often found most difficult. That feeling of the empty prayer, as though either there is no God to hear it, or (more often in my own case) that it is not sincere enough to reach Him, can be crippling and frustrating. I have, however, found it increasingly helpful when that happens simply to pray about it itself. If I don't feel like I'm making a good connection to God in my prayers, sometimes it helps just to confess precisely this and entreat God beyond it.

In two entirely different sources I have found helpful content on this matter. One case is a moderately popular bit from C. S. Lewis:

I have a notion that what seem our worst prayers may really be, in God’s eyes, our best. Those, I mean, which are least supported by devotional feeling and contend with the greatest disinclination. For these, perhaps, being nearly all will, come from a deeper level than feeling. In feeling there is so much that is really not ours—so much that comes from weather and health or from the last book read.  C. S. Lewis, Letters to Malcolm

Lewis, here and elsewhere, stresses the extent to which obedience in spite of contrary feelings can be something of more substance than a gay and easy submission. Our feelings come and go and change like the wind, often for reasons no more spiritual than precisely the weather. Yet the devotion to, well, practice devotion to God in spite of this means something, and God may well find that itself pleasing.

Lewis also often emphasized the partially related point that our prayers are not, at root, meaningful from our own words or thoughts or intentions, but rather from the Spirit at work in us, in a way that transcends and perhaps relativizes our own role. The goal in prayer isn't so much to muster up our own great offering of praise and supplication to God, but rather to participate in that speech of love that God already has within Himself, as the Holy Spirit cries out in us. As Lewis says in Mere Christianity:

An ordinary simple Christian kneels down to say his prayers. He is trying to get into touch with God. But if he is a Christian he knows that what is prompting him to pray is also God: God, so to speak, inside him. But he also knows that all his real knowledge of God comes through Christ, the Man who was God — that Christ is standing beside him, helping him to pray, praying for him. You see what is happening. God is the thing to which he is praying—the goal he is trying to reach. God is also the thing inside him which is pushing him on—the motive power. God is also the road or bridge along which he is being pushed to that goal. So that the whole threefold life of the three-personal Being is actually going on in that ordinary little bedroom where an ordinary man is saying his prayers. The man is being caught up into the higher kinds of life—what I called Zoe or spiritual life: he is being pulled into God, by God, while still remaining himself.

He also addressed this subject in a poem:

Master, they say that when I seem
To be in speech with you,
Since you make no replies, it’s all a dream
—One talker aping two.

They are half right, but not as they
Imagine; rather, I
Seek in myself the things I meant to say,
And lo! the wells are dry.

Then, seeing me empty, you forsake
The Listener’s rôle, and through
My dead lips breathe and into utterance wake
The thoughts I never knew.

And thus you neither need reply
Nor can; thus, while we seem
Two talking, thou art One forever, and I
No dreamer, but thy dream. C. S. Lewis, "Prayer," Poems

One final consideration from Lewis is the way in which our prayers on their own have a blasphemous and idolatrous tendency. When we pray to God, we nearly always address, on some level, a mental prop. We have an idea of God, sometimes a physical pictures, other times a philosophical one, or whatever else, that hardly matches His reality. On some level, we willingly entreat this imaginary deity even when, on another level, we do wish to address the true God. So he considers that, by Christ and the Spirit, we may ask God to transcend the mere words and ideas in our prayers to make them right. Per another poem:

He whom I bow to only knows to whom I bow
When I attempt the ineffable Name, murmuring Thou,
And dream of Pheidian fancies and embrace in heart
Symbols (I know) which cannot be the thing Thou art.
Thus always, taken at their word, all prayers blaspheme
Worshipping with frail images a folk-lore dream,
And all men in their praying, self-deceived, address
The coinage of their own unquiet thoughts, unless
Thou in magnetic mercy to Thyself divert
Our arrows, aimed unskilfully, beyond desert;
And all men are idolators, crying unheard
To a deaf idol, if Thou take them at their word.

Take not, oh Lord, our literal sense. Lord, in Thy great,
Unbroken speech our limping metaphor translate. C. S. Lewis, "Footnote to All Prayers," Poems

So, once again, we do not pray as we ought, in heart or mind, but by God's mercy, through the Holy Spirit, we may ask God to see past our pathetic, compromised prayers and hear whatever is good in them as it rightly ought to be.

This, then, brings me to Anselm. In a book of medieval prayers, I found this included in a prayer he wrote asking God to bless friends:

And though our prayer is cold, because our charity is so little fervent, yet Thou art rich in mercy. Measure not to them Thy goodness by the dulness of our devotion; but as Thy kindness surpasseth all human affection, so let Thy hearing transcend our prayer. St. Anselm, "For Absent Friends," Prayers of the Middle Ages: Light from a Thousand Years

And this, this hits the root nerve. I may find myself praying with a cold, compromised heart, but must I not ask God to look past even this? Though my charity is so little fervent, though my devotion dull, can I, must I, not beg God, on the grounds of His own surpassing kindness, to bless my friends in spite of myself? It seems the only way, as my prayers themselves can merit nothing.

Lord, ignore every word I say, but grant my plea.