[ He genuinely didn't mean it as shade to imply she hadn't gone there. He just assumes she must've gone there a bunch to know it so well. So, he completely believes her when she says she's gone a few times. ]

Yeah, I guess so. I live in Tokyo so it's more about going to Shibuya or Ikebukuro or somewhere like that.

[ But! He's trying to expand his horizons! And he wants to take Wednesday out somewhere ~~~special~~~. ]

So. Zoo, castle, shopping. Sounds like a pretty good date.