"Let's put it this way," Sam said, lightly, "I haven't used up my nine lives." He had, truthfully, lost track. He usually counted only three: the very first time, when Dean had sold his soul to bring him back; the second was when he'd gone to heaven; and the third was when he'd jumped into the pit. But there had been a few other times, too. When a girl had made a wish on a cursed coin for him to be dead. When he'd gone to the past and been stabbed with a pipe, then restored by Michael. So, the real answer was probably that he'd died five times, and come very close on multiple other occasions-- maybe close enough to count by some standards, he didn't really know.
He tightened his arms around her and rested his forehead against hers, running a hand (comfortingly, he hoped) over her shoulders. He felt better for having told her all of this, and for the fact that she was still here-- but she felt worse for hearing it, as he'd known she would, and that made him feel awful. "I've seen and done a lot of things that shouldn't have been possible," he said with a slight smile. "It was like... I'd been put back together, but a piece got left behind. You don't need your soul to be alive, but you need it to be... you."
Describing what it was like to be soulless would be very difficult. The feeling of being hollow, which he'd filled in with the desire to hunt. It was the only thing he'd understood, really, the only thing that made sense; that the world was full of monsters and he had a job to do. Everything else had been clouded by sentiment. His mind and his memories had been intact, so he'd remembered why he'd felt the way he had, and he'd been able to fake it to an extent, but he'd felt none of it. Without his soul, the only thing that had mattered was survival and destruction of the monsters he came across.
He looked at her, directly into her eyes. "You don't have to worry about my soul, Jess. I went through all of that, and I survived it. I'm here and alive, soul and all. And we're almost there, almost through the worst of the things I've done and been through. There's only one thing more, really, but that can wait." He pressed a kiss to her temple, raising one hand to rest against her cheek. "Let me help you work through it, okay?"