No, Ray hadn't been there to witness any of John's sins. He didn't know a majority (if any) of the details. If he had there was a chance it wouldn't have mattered too much. Ray may have been a little too judgmental in his past. He'd been a little too narrow minded about the former criminals on his team. They'd more than proven themselves but, even before then, he had been trying to find the good in them. It was likely he would've done the same with John and had been all too happy on the occasions when John did something to validate that belief.
He'd seen the good in John now. There was no changing his mind. He'd continue to tell the other man, too. As many times as he needed to hear it.
"When you want them to be." Ray shot back. He wasn't arguing though. He didn't come here to argue or plead his case. This thing between the two of them, whatever it may be, wasn't his decision alone. John had a say in it. As long as the other man accepted that Ray had made his choice he wouldn't argue John's own. He just wouldn't accept the idea that a 'no' was for his own protection. He'd rather the other man say he wasn't interested. He was fully expecting something more along those lines. It took him a moment to realize that John had gone the opposite direction.
"You would?" He asked, eyes a little wide as he mind tried to play catch up with what had just happened. Once it sank the smile he flashed John was bright and genuine. "We can definitely keep things simple." He said before rethinking it and allowing his smile to turn into something a little more sheepish. "Though... you may have to let me know what you are and aren't comfortable with." Because he knew himself and he knew he could get a little carried away.