I never said you said he was a stalker, if you look up I was replying to someone else when I said that.
No... sending one email or text saying: "hey, I'll be in town during this dates" it's called normal business.
Texting about a potential overnight IF he (the escort) goes to @adventurous old guy 's town is being proactive and I'm sure he's doing it to others trying to find an anchor (someone who will hire him for an overnight, multiple hours or pay his airfare) to make a trip worth it. I'm sure he's texting others too.
Desperation, that's a different level.
Stalking, also that's a another category.
I hate how so many words (specially adjectives) have become synonymous now a days.