The word ‘ashamed’ is translated from a Greek word that means disfigured. It's that kind of shame.
That is the tragedy with rebellion. We are ashamed to be Christ's. What an insulting attitude! We think so little of the Lord, that we would be ashamed to be identified with him. The one who is our Creator and our Saviour: and in our perversity, we are ashamed of him. We insult him. We look down upon him. We hold him in contempt. We think that the Lord Jesus and his religion is inferior to a life in this world, and we would be ashamed to be Christians. This is what the Lord says. If that is our attitude then we need to hear these words: ‘Whosoever shall be ashamed of me and of my words, of him shall the Son of man be ashamed, when he shall come in his own glory.’
Here is the difference. The truth is that the Lord Jesus Christ – when he comes in his glory, and he sees hundreds of thousands, billions of people who held him in contempt – will be ashamed of them. Not in a retaliatory way; it won't be cheap retaliation. He will be ashamed of you and I, if we are lost souls, because we deserve it, because we are contemptible. He will look at all those who rejected him – those whose heart strings he pulled and pleaded with them – and he will see them in that last day in their sin: unwashed, failures, rebels against him. How foolish you were to reject the Lord of glory and his love and his salvation, and you puffed yourself up in pride, and said, ‘No, I'll hold that in contempt. I'll have my own life, and I'll do it my own way.’ Of course he will be ashamed of you. What an insulting attitude to God! What a fleeting life! And now you face all eternity and you've squandered it all away. Of you will the Son of Man be ashamed.