Lauryn
"Does healing not work?" He muttered, his suspicion rising once more as he seemingly got control over of his scales and blended some scales to his surroundings, only getting a few details off. He took a few steps to his left, seeing a full clearing he could take that would make it hard for others to follow him. His wings were pulled close to his body by now, with his back legs taunt for a leap. 

"Why know me- my story? Why want?" He seemed to pick up a little bit from how Milkweed was talking, he was certainly a fast learner. He could hear that the dragon was... Doing something he hadn't heard before. A tone in their voice, their behavior, it was nothing like he had ever seen before. He could take it in two ways: it meant they did mean to help him, or it was a way to get into his skin in a very, *Very* Bad way. The way to determine that, was unfortunately, was allow them to get supplies they promised to bring. He seemed to nod faintly, as if he was giving them a silent permission to go gather supplies and such. He wouldn't move unless he saw danger coming with Milkweed.
Napoleon
A worried, pained expression as if the leafwing had flown into a bush of rose thorns filled his face as Tragedy's suspicion and mistrust only seemed to swell - he figured at any moment now - he'd bolt and never be seen again... That fact seemed to scare him the most due to his ambiguity. "H-healing with medicine *Does* Work - it's just - going to take some time is all." He nodded with a weak smile, hoping to reassure the sickly looking dragon before him - even if it was only enough to keep his talons planted in the first in front of him and out of the sky. 

"I want to know because..." He thought - for him, it was a subconscious desire to do good for another dragon, it wasn't really something he put actual thought behind in the heat of the moment. "Because no matter who you are... No matter what you've face, your story deserves to be heard." He frowned - the thoughts racing through his mind at just how many dragons might've been in a similar situation to Tragedy, only for their names to be washed from the scroll of time entirely. "No one deserves to be forgotten- and nobody deserves to suffer as you have." He was impressed by Tragedy's ability to learn - it gave him a glimmer of hope that maybe... *Maybe* This dragon could successfully be reintroduced to modern dragon society- well... If that was something he *Wanted* - Milkweed wasn't going to force that decision onto him- though he was going to continue to *Try* To be his friend regardless of what Tragedy chose. 

Milkweed smiled with relief and nodded thankfully to Tragedy- walking a decent distance away before taking off into the blue sky - walking first to ensure he didn't spook Tragedy any further.
Richard
Smol timeskip? I would assume it would take a little bit before he returns?

Can you set it up? I wanna spook Milkweed