Saint Chrysostom says: “Notice how, from the very beginning, he defends himself before him for not coming to see him. The words ‘until I come,’ and again, ‘I hope to come to you shortly’ (cf. 1 Tim 4:13; 1 Tim 3:14), had made him expect his arrival soon. Therefore he immediately defends himself. Yet he does not at once state the reason why he did not come, so as not to grieve him too much. The reason was that he had been detained by Caesar, Nero. Only at the end, when he invites him to himself, does he reveal it. At the beginning he does not grieve him, but expresses his desire to see him.”
By the words “longing to see you,” he leads him to the thought: “Could I have voluntarily deprived myself of the pleasure of seeing you, if I had been able to come to you?” (blessed Theophylact).
“Remembering your tears.” The Apostle wished to see him not only because of his own love for him, but also because of Timothy’s love for him. Timothy showed this by shedding tears, probably when the Apostle left him and took leave of him.
“The Apostle shows here that he does this, that is, prays to see him, not simply and not without cause, but, he says, ‘remembering your tears.’ When he parted from Paul, he probably wept and sobbed more than a child taken from the breast of his nurse and from milk” (Saint Chrysostom).
Remembering this, the Apostle says to him, as it were: I long to see you because I love you. “But even if I were extremely unfeeling, harsh, and inhuman, even then I could not fail to have such a desire, for the tears of yours which I remember could soften me” (Saint Chrysostom).
Therefore, when the Apostle then says, “that I may be filled with joy,” he at the same time suggests: that I may also dry your tears. Saint Timothy’s tears could not fail to awaken deep grief at their separation in Saint Paul’s heart as well. From this naturally comes both the desire to meet and the foretaste of joy in both.
Ambrosiaster writes: “The Apostle assures him that he remembers Timothy greatly and thirsts to see him because of the remembrance of his tears, which he shed from love for the Apostle when, as is understood, the Apostle was departing from him. Therefore he does not without cause desire to see one who loves him so greatly, so that he may be filled with joy from their mutual rejoicing.”
By all this the Apostle testified to his exceedingly warm fatherly love for Saint Timothy.