Just found your second webcomic... am all caught up and loving it so far! I like the detail on the period clothes in this pic.
I'm a big history buff so I will take some guesses at locations/dates...
Top) 1880s-1890s, South Africa or Jamaica. Patrick looks more of African descent than South Asian, and she looks like a cane-cutter. But didn't they mention a war in the comic (Boer Wars)?
Bottom Left - 1700s, Italy (possibly Spain or Greece?) - I'm basing my guess on the buildings and columns in the background, and Patrick's dress and hair, which seem more Mediterranean in contrast to Kara Lynn's English dress & bonnet.
Bottom Right - Middle Ages. I'll guess sometime during the Hundred Years' War, with Kara Lynn being the English boy and Patrick fighting for France... definitely no poodle.
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