Hiccup & Toothless & Erik
"Does that mean you're willing to let Toothless come along for lunch?" The backyard was certainly big enough for it and he could play with Aurie while they played chess. The weather would only get colder, so it might not be entirely feasible, but he wanted to immediately find other avenues for them to all spend time together. Toothless would see that Erik was trustworthy. Hiccup would make sure of it.
As the conversation turned to Tefe, he learned more about the other woman and looked at her curiously. She appeared to be human, but if she wasn't then he could absolutely understand why she might hate humans. People were cruel when it came to things they didn't understand or felt threatened by. Madison Valley was like that in fewer and fewer cases these days, which he was grateful for. Otherwise having the dragons would be problematic at best.
"This is a good place to learn such things, even if it can be painful." Loss was always painful, no matter when or where they were. Hiccup wanted to be more comforting in some way, so he leaned in a little so that their shoulders were touching for a brief moment, a reminder that he was still here at least.