If Dylan came face-to-face with the girl he was secretly in love with during NBK, he would’ve…..yes, let her go.
As Dylan mentioned in his draft version of the love letter in his journal:
”..if you tell me to leave you alone, I will. I like you [redacted], but I won’t force that ever.”
Granted, this is not quite a comparable situation. 😉 But in a way, it is. It speaks volumes of Dylan’s code of conduct with his Object of his Affections. Dylan wouldn’t have selfishly forced the situation if he ran into ‘his love’. Ultimately, he wanted the girl that he put on a pedestal to return his love of her own voalition. In his imagination, he thought of she and him both wanting the same things equally and that they as partners would be willing to end their suffering, loneliness and misery by ending their lives together. If Dylan had the misfortune of running into this girl during the massacre – and it would be very tormenting for him to have that happen – it would have put him in a predicament he wasn’t quite prepared for. For one thing, in theory, he had not sent her that love letter so she wouldn’t have even know that he had these devoted feelings for her. She would’ve met his gaze with a look of shocked recognition in her eyes that would’ve silently pleaded “Dylan?? What are you doing?!” I tend to think Dylan would have lost his nerve in that moment.
During the massacre, he ran into Tim Kastle between the ceiling boards of the Common’s kitchen area and what did he do? He signaled silently for Tim to leave as they were staring at each other for a couple of seconds from across a distance. But this wouldn’t just be a friend of his like Tim was, this would’ve been the supposed girl of his dreams looking back at him fearfully,. in a way that ultimately would’ve been understood as rejection of him. I do not believe he would’ve taken it upon himself to act selfishly in that moment and put his desire to have her with him in death, to force her to go with him. I think he could not be happy with himself in leaving this world, into the Halcyons, knowing that he had forced her against her will to die and she, in that moment, did want to give up her existence for him of her own accord. If he had forced her to die, he would likely have ended his own life in a very miserable way immediately thereafter, abandoning NBK with Eric.
So, yes, I think Dylan would’ve let her go. Dylan understood that that he couldn’t force a love, he wanted his girl to be willingly his. True love could only be genuine in this way. As Fate decreed, he would die on his own at the end of Judgment Day and wait for the love that was to be his on the other side.
“I will be free one day, in the land of purity and my happiness, I will have a love, someone who is me in a way. Someday… Possibly thru this life, maybe another, but it will happen”
"As I look for love, I feel I can never find it. ever. but something tells me I will. someday. somewhere.As my love will find me, She feels as I do right now, I can feel it, she will be inseparable, Her & I. Whether it is [redacted] or not, I think I’ll find it.”
I’ll be here just waiting for you
I’ll be under your stars forever
Neither here nor there just right beside you
I’ll be under the stairs forever
Neither here nor there just right beside you
— Smashing Pumpkins – Beautiful