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So I got confused and messed some posts up but I fixed them again. Danbooru says Diletta is just an artist, and when I checked the other associated artists they weren't listed as being part of a circle called "Diletta". I got frazzled and stopped changing things and just undid...what I changed. No harm no foul, right?
Based on Today's episode, I would be pretty comfortable saying these characters are from the show "Hige wo Soru. Soshite Joshikousei wo Hirou"
They don't seem to be related. That anime and this doujin. This is something about a couple in a long-distance relationship, and the girl went off to Tokyo for uni first because of a one year age difference, and he promised he'd go to the same uni as her. That's the bare minimum I can gather from Google Translate.

Here's the product page on DMM:
Fair enough, seems like it's just an extreme coincidence in character design.
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