This reply is overly harsh. He is not boasting, and the tone of your reply is warranted for someone who is boasting. On the contrary, he is doing the opposite a

This reply is overly harsh. He is not boasting, and the tone of your reply is warranted for someone who is boasting. On the contrary, he is doing the opposite and saying that he feels like a loser, to put it bluntly. He seems very distressed, sad and defeated.