Email email when date is free

I’m trying to create a waitlist automation, where it’ll send an email to a person when the date they want is available.

I have a form view set up, and a table where all the submissions go. Within the same base is a table where reservations are, I want to create an automation that looks up the dates in the waitlist table and if any of those dates are free, it will email the person connected to that record.

Seems like it should be easy, but I’m not seeing it that way. Does anyone have any insights?