My novel "Strongbow's Wife" contains a scene in which the (real) female protagonist meets a young man who writes poetry and is working on an epic poem. One reader asserted that this could not have happened in the 13th century. I had to point out that the individual was a real person. I have no evidence of the two meeting but he was a protege of her husband's uncle so it is as likely as not.
I wasn't aware of the Tiffany problem by that name but this seems like a typical example of the phenomen.