That is really cute. Very "Jack and Jill magazine."
I think it's fairly contemporary, but what I loved about it is that, yes it does look like you describe it. Unfortunately, I'm one of those people who often pulls images and forgets to note who they are from, or by, and then when I try and track down where I think I found them, I can never find them again. Hopefully someone else will recognize this and chime in with who the artist is.