I'm gonna go out on a limb here... I'll admit, the dinner invitation to the crazy bitch's house was a little weird. Was there any indication that he attended?
As to the pizza-related map on the handkerchief thing, is it possible that a man born to Italian and Greek immigrant families that grew up in Chicago really likes pizza and pasta? And that the map is referring to a tomato-based sauce stain that resembled a map? Or maybe map was a type-o or an autocorrect. Reading the email thread, it looks like he was visiting some folks that had a vacation rental in Martha's Vineyard and the cleaning people found this handkerchief, contacted the folks who rented the place and then they forwarded it to him to ask if it was his.
I've been following the Reddit thread on this and I think people just might be getting trolled. It seems odd to me that there really isn't anyone jumping in like Zippy does and trying to set them straight.