Trust me bank tellers don't care what you do with the money you withdraw. They are not calling LE and telling them that you just withdrew several hundred dollars and asked for large bills. Relax.

As for the gal's preference all I can tell you is that no girl I have ever seen has stated one. I see my ATF a couple of times a month. Most of the time I pay her in hundreds, sometimes in 20's and 50's.  She doesn't seem to care. As long as the money didn't come from a monopoly game I doubt any lady will.

Less paper bills to handle for both you and her of you stick with Ben Franklin. There is an old gambler's fear that Grants are unlucky.

Another newbie here (been lurking for a little while now) and could not seem to find this across the first few pages of this forum, nor through search.  In what denominations does a provider prefer (I assume for the very high end she'll want Bens, but in general - and specifically those I will be seeing as I begin to step into the hobby, will most want a combination of Bens and Andrews or just Bens)?  

With concerns of being discreet and keeping the profile low, I can see how larger denominations may not cater to that (most ATM's dispense Andrews, and requesting larger bills from a bank teller obviously adds to tracks the trail).  However, I do understand that providers wouldn't want to carry around that amount of physical paper after an appointment.  My apologies if this question is too absurd - I'll chalk it up to being that guy in history class asking all the stupid questions.  

but the later in the evening it gets, the better Grant and Andrews look to me. If I want to go to the hotel restaurant, I'd rather not pull out Ben (I don't eat THAT much and I don't drink, so Ben feels too conspicuous). If I want to visit a local Dutch Bros. and I haven't had time to break a large bill, then I'm SOL for the coffee.

Other than that, I've never told anyone either.

and never had a request either for specific bills.  I usually take 50's.  I think they would be easier to break than 100's.  I make my w/d's at the bank in person, and I have never had a teller make a comment.  IMHO, that would be totally unprofessional on their part, and besides, it's none of their damn business anyway.

Swim

Just tell her that you are headed to an antique flea market sale.

This is what I do, as the teller at my bank is someone who knows my company and family.

I'm known for going to buy jewelery at these things, so it makes for an easy cover story.

Dealers at these shows do accept credit cards, but offer discounts of up to 10% for cash, for various legit and illict reasons; so cash is often the currency of choice at these.

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As long as it is accurate I do not have a preference.

all kidding aside....I always use big bills, so that a quick glance at the envelope can confirm it is all there.  I try and give the lady a moment in private to check the envelope, while I use the restroom.  It would be a real turn off for me to walk out of the bathroom and see my date flipping through piles of 20's trying to make sure it is all there.

...in case she needs to buy gum.

I really don't have a preference, sometimes some small change can help, like a mix of hundreds and smaller bills. I once had to keep a cab driver waiting outside a store while I ran in to break a $100 to pay him.

Thanks everyone for the input!  Sounds like it won't cause too much drama either way.  The responses are much appreciated.

There are some who think $50's are unlucky due to the fact that Grant was a supporter of the unlucky Confederate States...

Popular Gambling Superstitions
Many gamblers feel that it is unlucky to enter a casino through the main entrance. Years ago the MGM in Las Vegas was themed after the MGM film studios and the main entrance was through the mouth of the large MGM lion. Many superstitious players would not enter the casino by going into the mouth of the lion. They considered it a double curse to walk into the mouth of the beast along with the fact that it was the main entrance to the casino.

Many gamblers believe that $50 bills are unlucky and they will not accept being paid with them. There are several casinos I have visited that do not give out $50 bills from the cage when players cash in their chips. The casinos that do use $50 bill often find that gamblers will refuse them as payment. Some people also regard the two dollar bill as unlucky and this might explain why the numerous attempts to bring them back into general circulation have failed.

and this was a copy/paste from some internet info.. Not my own words but I have heard these statments before.

glad to have helped!!!!!!!