I dated an IT gal once who's favorite saying was "in the world of electronic telecommunications, every thing is possible with enough money and time, and sometimes you can buy time with money!"
Think of this, with cameras being ubiquitous, you are tracked almost 24 / 7- and face recognition algorithyms make automated recognition a thing of reality. Then we have the cell phone which can triangulate your position to within a foot or two.
While our government tells us that no one has access to this vast sea of meta-data, there is great potential for financial gain for access to it - detective agencies, consumer profiling, job clearance investigations, etc. The data collected will eventually (if not already) be sold for financial gain, and lets face it, once that happens, if someone REALLY REALLY wants to know where you were August 23rd 2013 at 1:30 AM, for a price, they can find out.
If I had an SO, and I were to go to a meeting with an escort, in today's world, I would,
1) build an airtight alibi for my periodic absences (out of town client, off site meeting etc.) where I would also have a reason for not being available for texting or phone calls.
2) I would obtain a hobby phone which would not be traceable to me, and woudl be billed to me at either a PO box, or work.
3) I would leave my non-hobby phone wherever while out on a "date," it would be set to have a message "this is john, I am unavialable to take your call right now as I am (in a meeting, in the lab, working on a contract, presentation, business proposal, study plan etc.) but when I am free I will give you a call. Thanks for your understanding"
4) I would inform my SO of the pending meeting, lab activity, work on contract etc... and tell her to not call me then.
5) Leave my hobby phone (when not in use) someplace where it would be inaccesable to the SO.
6) when the hobby phone is NOT in use, turn it off, and remove the battery.
but way before that, I would ask myself - I've got a hot SO, she loves me, so why do I feel compelled to do this?