If he did share, Dean would realize how freaking disastrous this whole thing has gone. However, he acknowledges it's a disaster even without that detail. Dean is glad that Sam takes the time to consider his answer and to think through everything that he just said.

Dean sighs and watches Sam, giving him a chance to finish. "Dude...I hate to point it out, but we're dead. She's not and visiting hours aren't exactly a thing so there aren't going to be any conjugal visits for you two. You're not even supposed to be doing the letter thing. That's---I'm not sure Jack or Cas were being fair big picture to let that happen. I'm not saying get over her. I'm just saying..." Dean stops because he knows Sam well enough that he knows this is going over like a wet blanket. "Fuck. I don't know what I'm saying. I don't think you have a lot of options. We can try talking to Jack. See if some big gestures will at least get Ruby to talk to you. Maybe you two can work some sort of agreement out that way."