Search one dataset to return data from another dataset

I am trying to setup a query to look at one dataset to review a date and if that date is not used for an item, it will return the information about that item to them in a repeating group. Is there an easier way to do this without making something convoluted that will end up failing in the end?

Some of the data I will be using is the Date and time that the item is booked for,

Some of the information that will be returned on failure to find a booking is size, color, pictures and business information for the item

Please assist.
Thank you!

Sounds like you have a data type called ‘booking’ with a data field of Date as well this should have a data field of ‘item’ as well. So, just simply do a search for bookings with constraint for whose date is empty, but your RG will be set to type item and the datasource dynamic expression that is the do a search for bookings will end with each items ‘item’.