That's true, I imagine they have crossed paths! He has a bad/intermittent/pretend bad memory though so he can easily pretend that they've never met before, which can maybe excuse their network interaction.

I imagine he knows he's around. She definitely seems like she'd be a useful asset, with her medical skills and willingness to go under the table. He'd definitely be interested in her sticky fingers, and to know her Council contacts. Maybe this is the 2nd or 3rd time he's put out feelers? He doesn't really get mixed up in Irkalla stuff, but he'd be curious about what she thinks about it and how it affects general attitudes, the black market, etc.

Maybe at some point, if he builds something cool, he'll try to use her as a fence!