There's never really any right time to leave or any goodbye that will make you feel less alone after someone leaves. I remember freshman year absolutely resenting my boyfriend at the time for leaving and not saying goodbye. He just packed up everything and left, went to another country and then another. When we finally saw each other again, I understood. Goodbyes are just too hard.
And now it seems strange with my current boyfriend gone. We said two goodbyes, the first was honestly the most heart-wreching, gut-pulling, nauseous goodbye, because it just hurt too much. He forgot something and had to come back, the second time was better, in my head we were just hugging until next time. Next time being 3 or more months from now. But, I am actually doing a lot better than I thought, I guess it helps that I have never associated any songs with him or with us. Which was always the hardest part for me, after a break up, a passing or a goodbye the songs that I associated with them seemed to play on loop. Which is just awful because how can you not get sentimental?