I have not ordered the square reader yet as I don't know how and I don't know how to work it. I am not very good with computers either!
The chip reader will connect bluetooth to your phone or ipad. Open the square app and go to Setting/Hardware/Square readers and it will walk you through pairing it. If you have a Square stand you can just plug the USB cable into the USB hub and it will connect like that and keep it charged.
Square Community
Square Products