There is nothing in your list that would get you denied entry.
The OTC medicines should be in their labeled packaging/boxes (and not loose pills). All the medicines you mention are available OTC in Dubai as well, so you do not need a prescription with you.
Dubai is fairly liberal, I’ve been there a number of times and never had any issues with Customs. Always had condoms, some medicine, and a tablet with books/photos/whatever. Your luggage is scanned by Customs, but that’s all.
Officially, Dubai customs has a web site, but the list of prohibited items (at bottom) seems to be mostly typical.
About 20 condoms (I’m single)
A socialist political magazine I picked up in South America
A Kindle with various books that may be considered offensive to different people
About 50 little plastic pill ziplocks
This should be fine unless your books or magazine “contradict Islamic teaching”, whatever this means.
Over the counter medicines (Aleve, Benadryl, Lortadine, Simethicone, Melatonin)
Those may be a problem. Especially OTC medicine, it is hard to say if any of those contains a substance prohibited to import in UAE.
Hemp clothing with small pot leaf symbols on the tags
No idea at all; certainly not in the banned list, but one never knows.
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