Finding a local guide in Okinawa and/or Tokyo

I’m traveling to Japan for the first time in December. Splitting time between Tokyo and Okinawa.

What I am looking for:

I don’t want a polished tour guide. I would like a local to just hang out with and see some of their favorite spots. I’m happy to pay for their time and pay for meals/drinks/activities. So yeah, reading that, basically a date but completely platonic.

It could even be more than one person. In that case I probably wouldn’t pay them but would pay for everything for our “group” for the day.

I’m learning Japanese, Pimsleur every day. So at best I will know basic conversation. It would be best if they knew intermediate English, but I am happy to stumble through with translation apps.

Any recommendations?