Yes! A couple of weeks ago I had 2 of my normals (I think it was Chevre and Lolly) having a conversation where they discussed what gift to give to another villager.
Yes, since I have two each of 5 personalities it happens a lot. Their conversations always seem to be positive, which makes sense since their personalities are the same.
Marshal and Raymond were chatting and syncing up with the cutest little twirl and sparkle! The chats between the same personalities are actually really adorable bc they just click with each other
Tangy and Ketchup (AKA Tangy Ketchup) get along great which worried me because I was weary of having two of such a vibrant personality.... so far it hasn't been too bad
Long answer, smugs rendezvous at night or shortly near dusk. I'm kind of interested in getting 2 of each personality types on my island at least one time to unlock all that juicy dialogue. But screenshots/videos are just as neat so I digress.