I think you’ve been incredibly unlucky. I’ve had trouble falling for Julian in town in my Charm Sub run.
Weirdly enough, I succeeded on my first attempt against Julian, and on all three checks so far to extort the thief you can find while exploring the storefronts in town (all are C+ checks)
I'm fairly sure not all checks are rated the same though (having wayyyy too much trouble gathering materials in the forest despite literally never failing on the leopard encounter, and both being normal P or W checks), so it's worth considering.