Dean couldn't help but to chuckle at the flush on Dempsey's cheeks. He took it as a good sign. They really weren't very good at this deep discussion sort of thing, but it seemed to be getting incrementally better as time wore on. Still, Dean would rather be proactive than reactive if he could.

"Do you want to think about some," Dean had to choose the right word here. "Boundaries?" He thought setting some expectations might help prevent some future disappointment. Boundaries set that clear limit. He already felt a little guilty for the whole thing with Thaleia, even though he hadn't done anything wrong. He didn't want Dempsey to get discombobulated because of something that could have been avoided. "Doesn't have to be now," he added, belatedly. It might warrant some thought beforehand, which was perfectly fair. Dean still wasn't sure what he wanted out of this personally yet. It would be terribly hypocritical of him to ask for monogamy when he wasn't always around, nor was he sure that he could commit to that himself. But if they put some more concrete thoughts out there and agreed on some rules, it might help.

He shrugged, still not sure what exactly they were doing here, but he did know he wanted to figure that out, so that had to count for something, right?