Yes, the language itself is customer facing. But exposing your objects (Liquid drops, Jekyll sites, pages, etc.) to your customers via Liquid is the responsibility of the app (in this case, Jekyll). It's not like the user of the language can just arbitrarily create lists of things that a incomparable (maybe you can in Jekyll, but that's not Liquid's fault).

Your expected result of this test is completely arbitrary. Why would something that doesn't have an "a" be the smallest item? Why would it be the largest? Or maybe it shouldn't be in the result list at all? Or maybe it completely depends on the specific use-case and there is no reasonable generic answer to this question?

Maybe I will understand the issue better if I know why some Jekyll pages have titles and some don't.