That's probably a good thing with some of the residents they have now. Lucy will also be quick to assure everyone that she's only protesting to go along with the bit. Lucy likes to think that anyone who's met Jack is a little less afraid of angels because while Cas can be intimidating (she's told; she's personally not intimidated by him), if you don't adore Jack, Lucy judges you hard.

Doppelganger gossip will, at some point, become old news. However, any version of Dean being single will always be hot tea. Oh, Lucy absolutely poked her nose in. It's sort of what she does. She should apologize for it, but she's not going to; she wants this version of Sam and Ruby (and everyone really) to know that they're cared for. Besides, she likes social events and weddings are her favorite. At least Sam is following Dean's lead on not making this an argument yet still picking up on what he should have done. Maybe next time he has a big life event, he'll tell Dean before it happens. Really, they both need to realize that they should let the other one in their lives. This world is different from the one they came from and they can actually have a peaceful, normal existence for the most part. They ought to take advantage of that and repair some bridges.

Dean only speaks again after Sam says that it would be nice to see him there. He nods. "Yeah, I'll scrounge something up." Meaning that he will contact Lucy and see about getting into the clothing storage to see what's there. If nothing else, Lucy will strongarm the other Dean into letting him loan a suit, and Cas will play delivery. Lucy is nosy, but she's good at getting things done and ordering people about so that those things get done.