"Don't get disheartened when I do finally pass. Okay?"
Jack opened his mouth but, still, no words managed to come out.
After gaining more strength, rising in level, and unlocking new abilities, Jack felt more confident than ever in his ability to protect his party. Add the arrival of gods to the Leisure Guild and it amounted to Jack believing himself able to never lose a party member again, so long as he followed Daruun's advice.
Then this decision came to exist.
It was only made worse by the false sense of achievement that he felt while Tralon spoke so highly about his and Jack's greatest moments together. That only made Jack more desirous of creating those moments again, to share those moments while he was physically with Tralon and not present through a computer screen, while he could truly consider Tralon a friend and companion instead of a mass of pixels doing whatever Jack ordered.