My roommate informed me there is a non-insignificant amount of Ryuji/Shiho and Ryuji/Ann/Shiho fics, and I didn't know I needed this character dynamic until right this second.
He was a totally unconnected rando, but she would have a built in reason to want to help and support, especially if she already had an established interest in tech shit.
And let Yusuke learn from him. He takes a day to paint a skill card, but the Demon Painter can convert as many free tarot cards as you want immediately.
/drags them both into Wildcard Ann AU Land. Though that's probably overloading the party. Not sure if that matters...More party is more better.