You have to make them eager. It doesn't show the stuff like it does but you're likely just making them happy or scared instead if eager

On new game+? And they aren't level higher than you?

you gotta give them the answers that make them have music notes above their head!! to be more specific, the last answer needs to be one that gets music notes!!

if the last answer is a sweatdrop or an anger marker, they'll have a different reaction!!

Lol so many Futaba's answering me. Ok so idk if this is a NGplus this, but all I have to do it be like "Nah screw you I don't wanna talk" and they'll join me.

It depends on the shadow. Some of them appreciate smartass answers and some of them will get pissed or feel bad

I'm pretty sure the "screw you I don't wanna talk" option appears when you've already caught or fused that shadow before.

I see, thanks various Futabas for all your help.

Do Yoshida's Social Link...not only is it one of the best Social Links/Confidants in the game, but more relevantly, his Skills help take A LOT of the RNG out of Negotiations!