That comment resonated in Obi-Wan's chest like a loud noise in an empty auditorium. He tried to contain it, but life-changing moments of heartbreak had never been something he could close himself off from or mediate away. He'd come the closest to the darkside he'd ever been when Qui-Gon Jinn was struck down by Darth Maul, and Anakin's bitter betrayal and the loss of Padme Amidala had left him the kind of broken that he could never truly find his way back from. He rubbed his hand across his mouth as he let Bail's words burn their way through heart, and when he turned to look back at Organa, his eyes carried a kind of warm affection that betrayed far more than he might have otherwise wanted to reveal.
Bail, Kenobi decided, was certainly deserving of a second chance, or a gift at a longer life. Truly, he deserved it more than anyone else that Ben had ever known. Organa had sacrificed so much, had loved so much and never faultered in his devotion to the freedom and happiness of the galaxy. Of course, Obi-Wan had always been pleased that Bail had found happiness with an incredible, unparalleled woman. He'd never felt anything akin to jealousy at the life that Bail had chosen for himself.
But sometimes, in the cool twilight, when Ben sat and dusted sand from his hair and relaxed to let his sun-parched skin cool off in the dropping temperatures, when he thought about how his choices had brought him to this miserable planet and what other decisions he might have made, Bail's name was always one of the first that came to mind.
"A second chance? I wouldn't know where to start. I've made too many mistakes." He'd smile, sad, self-deprecating, and he'd reach over to place a hand on Bail's shoulder. "But you - you deserve everything you could possibly want. I'm so sorry."