[TOMT][comic book][1990s][US]

There was a book in my family bookshelves that had a serialized collection of comics, just pen and ink simple drawings. It was from the perspective of a girl that was a teenager in, I think, the early 70s, published in the early to mid 90s, but I'm not sure about that. There's a strip where the main character is visiting with a friend who has a pretty creepy and sad life as I recall, and she has a painting in her house with a kid with big crying eyes. The girl says that if you look at the painting and cry, it proves that you're deep. I think the narrator does something like putting water on her face to seem like she's crying. Does anybody recognize this?