@Digizel -- my thoughts are that, while Shieldwing doesn't take well to trickery or pranks, his questioning of authority appeals to Sylph. They find him annoying (the over-confidence, the arrogance) at times, but can recognize the common goals, and a friendship could grow there.
This does make sense. Although he doesn't question the authority or traditions so much as dislikes how hard they can be on him. He follows their traditions as best he can. Although, in terms of your Fellowships, that does give me an idea. One of Sylph's Fellowship questions are:
"You have helped ___ to question one flawed tradition of their House. Tell them what it was, and take a Friendship Gem from them."
Perhaps this could be in reference to Shieldwing. Perhaps Sylph came to him while he was frustrated or angry after getting a particularly nasty scolding for his attitude in a lecture on politics (perhaps they were even present enough to overhear him getting yelled at or something). They could maybe approach him, converse with him and comfort him a bit by talking about how the Brynbacks are too focused on being at the forefront of dragonkind politics anyway. And perhaps how this makes them come across as elitist, considering they're the only ones who actively teach this kind of thing as though Brynback being a superior House suited for leading were just a fact.
What do you think?
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In any case, these are my own Fellowship questions, so if anybody has any ideas of their own for these, let me know! These are all pretty easy to fill in, honestly, but I'd like to get some opinions from you guys as to which ones may or may not suit your own characters and their personalities. That way I could potentially go with the ones I think work best for each category. After all, you know whether or not they'd do these things better than I would. xD
___ has stood by your side in a fight against a monster of the Darkness. Explain how they exemplified your virtue. Give them a Gem.
___ was there when you were most vulnerable. Give them a Gem.