"I'm Crying Macarons" is a tag that you put on "Ib" fanworks that make you feel as if you're going to cry after looking at them.
Spoilers beyond this point
The tag is derived from the conversation taking place in the sketchbook world, wherein Garry promises Ib that if they escape the art museum, they will go to his favorite sweetshop and eat macarons together.
Depending on what ending you reach, it may be possible for them to fulfill this promise, but then again it may become an unfulfillable promise too.