Here are my thoughts regarding Skobeloff's Fellowship so far:

[@Digizel]
Shieldwing is a fellow prankster, a lover of tricks and jokes just like you. Explain how they once got one over on you, and give them a Friendship Gem.

(My thinking here is that Skobeloff, being a true and dedicated player of the Long Game, has developed something of a blind spot for the short term. This would allow the much more direct and straightforward methods a Warrior like Shieldwing would prefer to catch Skobeloff off guard.)

[@BleakBlueJay]
Sylph gave you their trust and confidence at a time when you knew you didn’t deserve it. Ask them why they believed in you, and give them a Friendship Gem.

(My thinking here is that Skobeloff and Sylph were partners in trickery back when Sylph was still with Myndoth. And when the Elders of Myndoth tossed Sylph out, Skobeloff couldn't find the courage to protest the decision. Despite them having every right to be mad about this though, Sylph forgave Skobeloff and the two are still friends.)