I've travelled internationally multiple times with around 10 grand and never once had someone ask about it.

 
As for your bank, they have the same requirement about reporting multiple withdrawals as they do large sums. The multiple withdrawals probably look more suspecious. Beetter to just get what you're planning on taking and just tell them it's for a trip you're taking. You don't need to get into all the details and if you're already know to the branch staff and they don't think you're a shady character they won't pry much.

TSA will ask you and unless you are a really good liar I would disclose the amount.  I am always honest when asked. You are spending the weekend with a lady friend. (true). Why cash? You don't want your wife to find out. (probably also true).  
What will you be doing? Going out to eat, visiting the sites, fucking. (also true!)  
As a Bonafide Hooker I deposit large amounts of cash, not withdraw, but I do make sure it is never over 10K at one crack. I also go to a credit union instead of an actual bank, which I prefer because I also am not a big fan of the government just like credit unions. Also a nice hooker hack is to make sure to go to different branches at different times with different dollar amounts on different days. Don't make the FBI dot connecter's job easy!!!      

I’m not so worried about traveling with it. But I would be too anxious and awkward about taking out that much cash at once.  Probably not the smartest thing to do, but I’ve done cashapp or venmo in these rare scenarios but only with trusted friends.

At $10,001, the treasury report is a requirement for the bank.  The bank also has the OPTION to file an STR for any amount over $2500.  Whether or not they do file the STR depends largely on your reputation with and relationship with the bank you are using.  If they don't know you or it's a new account, you are more likely to be reported.  It doesn't seem to be the case for you, but if you're DEPOSITING cash in any amount (even $100 or less) they will swipe your DL into the computer with the transaction record.  If you want to know the workaround, PM me, I'm not going to post it here.  (I'm inviting Huggy to PM, not hundreds of the rest of you.  Lol)

I would always keep that amount of cash in my pant's pocket (C notes). but with the new scanners, they insist you take everything out of your pockets first so I had the wad in my fist.   This was in Boston about 10 years ago.  

 
After going through, some agent (I don't think it was TSA) asked me to sit down in his "office" (tiny cubicle) and explain why I needed so much cash.   I was flying to Phoenix, and from past trips to Phoenix, I knew there were many antique malls on Scottsdale Road in Scottsdale and that when using cash, you get much better deals than with credit cards.   So I explained that to the agent and he seems satisfied with the explanation.   A lot of it has to do with your manner.   Don't freak out or get argumentative, just be cool and collected and have a good excuse to have the money.  My guess is that the guy was concerned about drug trafficking.   These guys are empowered to just take your cash and you have to fight for years to get it back.  

 
After that experience I decided to pay the ATM fee and get the money locally.   Not worth the risk anymore.

Assuming your provider really truly MUST have 10K in cash upon arrival for a extended weekend date (which is a whole other thread / discussion)....  

This whole business/universe of p4p & providers is fraught with risk, and requires a lot of ass covering and trying to anticipate, etc.   it's why it's still limited in scope and people, not many can handle or want to handle what's involved.   Some providers keep it as simple and limited as possible.....such as only doing incall with few clients at one specific location, or only doing outcall in one city oncertain days with select few clients etc.  This allows for risk and uncertainty with large cash amounts to be controlled somewhat.

In this day and age, why on earth would you actually carry 10K for any length of time to begin with...?  WHats wrong with other forms of transfer to mitigate or lessen the amount?    

it's not simply theft you need to worry about....it's a whole slew of possible scenarios (all of which are unlikely, but this is the kind of shit that only has to happen ONCE, and you have zero recourse..."you be fucked and out 10K" or much much worse)    A few years back, I had a associate who was returning from Vegas with 17K in his front seat in a bag.    He gets side swiped coming home near San Bernadino, flips his car off the freeway and lies in a twisted wreck....bleeding profusely, he had to be cut out of his vehicle.  It was a travesty.....much of the cash was either blood soaked or wet from the water they sprayed while cutting him out, and once the firemen saw all this cash, the cops there suddenly decided the cash was more important to focus on than saving his life.    Nothing ultimately happened to him legally because they were able to document that he won it in Vegas (although it wasn't all winnings, he had spent/lost a large amount, such that maybe 9k of the 17k was actual profit)    

He legal fees and retainers, to say nothing of his pain & suffering and other shit, ate up any profit......the point is, you never know what might happen.   What if you were suddenly stricken with a serious health problem, walking around with that money?      Either accept the risk as something you need to carry in order to satisfy your yen for sex & companionship, or regroup, rethink and try something else.

 
The Banks and 10K transactions.....they ultimately will NOT do anything to you unless you give them other reasons to do so......the US government agencies (IRS, FBI, DEA, SEC, ATF  etc etc) are so overwhelmed and understaffed that it's highly highly unlikely you'll be investigated unless you are really doing something worthy of investifating.

As Scarlet said, you don't have to make things easy for the pricks, but don't lose sleep over any of this either, or else you better do something else.

 
And I'd rethink the whole need to bring 10K with you to meet this provider.....it screams vulnerability, even if she is known to you.

I visit Vegas all the time with tons of cash. Now if you’re in a situation where you need to declare it you should.

I can't see why a SECURITY organization would have any interest in how much cash you have. On the other hand, Customs  can ask you to declare how much cash you are carrying when RETURNING the US (I haven't been asked to fill out a form on an international flight home since Covid). Unless you look like a drug dealer, the chances of being questioned are slim. The current Customs form (6059B) does ask if you are carrying money in excess of $10K.

I refuse to carry cash around because if you loose it then you are literally screwed. That's Why I tell clients that I use Cash App. When a Client pays you.......They can pay you through Cash App. and you don't have to worry about loosing your money. You can attach your bank account to the Cash App and then transfer the money into your account.  

Did somebody hit the lottery jackpot?    

I've worked hard for the meager money in my 401K.  Over 30 years to save for my retirement.    For most guys (blue and white collar) it takes 2 - 3 days of pay after taxes to raise the money for one hour of intimate entertainment.  Where is the inequality in that?   I'm guessing that Daddy died and left an estate to his son, who did the same and left the money to his son.   Now the grandson is literally blowing the easy money in an account he did not work for.  That seems to be the way the world works today.  For rich celebrities like Charlie Sheen and Donald Trump the dresser drawer has an envelope with $5000 inside that is what they consider chump change and earmarked... A Hooker and a Philly Cheese Steak.  $5000 to them is like $50 to the rest of us.

I fly regularly for business and carry several thousand on me.  I've never been stopped, but if I were my reason is I have a mistress and the money is to buy her gifts.  I can't use credit card since they can be a record of my purchases.  TSA agents don't care and it's a reasonable excuse, especially if you can act "embarrassed" about it.