Etiquette 101: On a Date with an Escort – What to wear, grooming, conversation, money

Posted on Posted in Ask Annie: Advice from an Escort about Escorts, Intimacy, Relationships, Sexuality, Sex Work, and "The Hobby”

This is the Part 3 of my answers to the list of questions sent to me by a young newbie. In Part 2 I addressed phone etiquette with escorts. Today I’m answering some of the questions he had about etiquette when meeting with an escort for the first time. I was eager to get to this one…


My fifth question is if I do finally hit gold. What is the etiquette on the date:

Can I just say I’m thrilled that this 20-year-old man is asking this? Somebody raised this boy right.

So let’s begin, shall we?

  • What should I wear?
  • Preparation: What to Wear to Visit an Escort

    Great question. There’s the old cliche of “clothes make the man,” but like all cliches, there’s an element of truth to it, albeit oversimplified. People judge us by how we present ourselves, and clothes and grooming are a huge part of that. And it’s not that people are shallow (thought lots of people are); much of this is subconscious. Since you’re already working with a limited amount of time when you meet with an escort, it’s probably best to start off on the right foot.

    You don’t have to get dressed up, but it’s best not to look sloppy. First off, wear freshly-laundered clothing. Actually, if you’ve been at work all day, it’s probably best to go home, bathe, and put on a fresh change of clothes. Jeans and a nice T-shirt is fine, but jeans and a nice button-down shirt is better (and can be more fun to take off). If it’s a hot day, think about fabrics–just say no to polyester, or you’ll be sweaty before you even arrive.


  • I haven’t shaved “down there” for a while, but what is the formality. Trim or bare?
  • Playboy magazine's Playmate of the Month for the June 1974.  Dare to go bare?  Hell no!
    Sandy Johnson, Playboy magazine’s Playmate of the Month for the June 1974. I’m pretty sure this was her centerfold photo. Check out that glorious bush!

    Should You Shave Before Meeting an Escort?

    Ah, see…this is a touchy subject, especially for me. I’m gonna try to stay off my soapbox, though.

    It’s really a matter of preference, and despite that fact that, at least in certain circles, “The bush is back,” I think that many people today have a weird aversion to body hair (especially “down there”). A lot of it has to do with fashion and trends. Fashion is cyclical. Just like clothing styles, trends in grooming (like hairstyles, facial hair, and yes, pubic hair) come and go in cycles. The full bush was big (pardon the pun) in the ’70s, as anyone who’s ever found an old Playboy magazine knows. Bare skin has been “in” in the world of porn for a long time, though it seems like that might be changing slowly but surely.

    Trends go in and out of style, and that’s to be expected, but what bothers me is that a lot of people are misinformed and they actually think that pubic hair is unhealthy or not hygeinic. This couldn’t be further from the truth. It’s there for a few reasons, but one of the most important ones is that it helps to decrease the friction of skin-on-skin, so that parts of us that rub together won’t chafe. And though removing it isn’t inherently unhealthy either, I choose not to remove mine and go completely bare. Shaving damages that delicate skin and can cause tiny tears and cuts, and I want my skin to be as intact of a barrier against infection as possible.

    There’s nothing wrong with hair. Some people really, really, really like it, and find a lot of hair to be INCREDIBLY sexy.

    As for me, I do not have a full bush. I do partially shave the general “down there” area, and I trim the rest very neatly. However, as you can see, I am NOT completely bare. I like the way it looks, and since the vast majority of my clients are older gents, they enjoy it too. That being said, there’s no denying that the completely hairless look has been the standard for a while (at least for women) and especially in the adult entertainment industry. Because of that, I think a lot of people–especially younger people–are a bit put off by the presence of pubic hair. So, you might want to play it safe: unless you enjoy shaving and it’s something you want to do, I’d just trim it very neatly to “clean it up.” I’ve seen bad shave-jobs, and that was certainly off-putting. But no escort is going to be put off by a well-groomed (but not hairless) package. Really, the most important thing is to clean very well with soap and hot water–whether you have hair or not–before you meet with a provider.


  • What do I say when I meet them?
  • What to Say When You First Meet an Escort

    “Hi Sally, it’s great to meet you! You look great. Thanks for meeting with me today!”

    Ok, you don’t have to say that verbatim, but I was new to this once, and I was also new to dating at one point, and I know that when you’re in a new situation, sometimes it helps to know what you’re going to say in those very first few seconds.

    Again, this may vary from escort to escort, but I know quite a few escorts, and we pretty much all agree that it’s really best to just be “normal.” There are no coded phrases or actions I expect a client to do when we meet. And what I’ve discovered after escorting for a few years is that the best clients are the ones who are simply genuinely nice people who respect me as they would any other woman they’ve asked out on a date. I’m a person. How would you attempt to put any other person at ease upon first meeting them?

    Well, you’d try to be normal, hence the “Hi.” “Hi” or “Hello” are normal, non-weird things to say when you meet someone, LOL. Then you’d give some standard social nicety (“It’s great to meet you!”). And you’d also do well to be nice. That’s where “You look great” comes in. Y’all know damn well we love compliments. You’re not gonna go wrong by complimenting a woman on her appearance, hahaha. This is a little more advanced, but you’ll do especially well if you compliment her on something \she chose, not something she was necessarily born with, like her cool shoes or her really unique necklace or something. This works best if you genuinely do like the thing you’re complimenting. Last but not least, thank her for meeting with you. This is something you do on non-escort dates, in meetings with professors, in meetings with employers and business contacts, and in various other professional and social contexts. Not only that, but let’s not forget that she has taken a leap of faith by meeting with you, and though it was ultimately her decision to do so, it’s nice to show that you appreciate that.

    At this point, one (or both) of you may want to make sure money is taken care of. Which brings me to your next question…


  • If it’s incall where and how do I place the money? Same for outcall?
  • How to Pay an Escort

    Here in the US, the exchange of money is a little tricky the first time you meet with a certain provider. You don’t know each other yet, so trust hasn’t been established yet. Providers have to worry about a lot of things when meeting with a new client, safety being chief among them. But as far as money is concerned, escorts may be thinking:

    • Why is he handing me the money? Why is he asking how much it would cost for (anal/a threesome/”just” a blowjob)? Is he a cop, or is he working with law enforcement in some capacity? Is he trying to trick me into offering sex for money, or accepting money for sex?
    • Is this guy going to shortchange me? Did he bring $X instead of $2X?
    • Does he even have the money? What if he doesn’t intend to give me anything?
    • Is he going to rob me? At the end of the session, will he jump up, grab the money, and run out?
    • I haven’t had a chance to go to the bank yet, and I have $XYZ in my purse. I really hope he’s not a thief. I better not let my purse out of my sight…

    Of course you, as a client, probably have very similar worries. This is why you do your research on a provider before you decide to meet with her.

    Check her website and/or ad. Many providers will have instructions re: what to do with the money on their websites/ads so that they never have to speak about it with clients on the phone, via email, or in person.

    If you can’t find that info, there are a few pretty standard methods.

    For outcall (the escort comes to you):

    You can put the money in an envelope and place the envelope in plain sight (like on the dresser) before she arrives. You can write her first name on the front of the envelope just to be extra clear.

    You can put the money in an envelope and place it in the bathroom. She will probably excuse herself to the restroom shortly after she arrives, either to freshen up, or because she assumes you have left the envelope in there for her. This method is preferred by many escorts because she can then retrieve and count the money in private and secure it in her purse without feeling awkward because she’s being watched.

    Some escorts like for the money to be laid out in plain sight (like on the dresser), but not in an envelope. This is because they want to be able to see it and count it quickly at the very beginning of the date so that they know that they’re not being shorted. Many providers have been burned by guys who shortchanged them significantly, but they didn’t realize it until they counted the cash in the envelope afterwards.

    For incall (you go to the escort’s location):

    Same as outcall, pretty much. Walk in and place the envelope in plain sight, and don’t really acknowledge it.

    The takeaway:

    Have her money, either in an envelope or slightly fanned/spread out, where she can see it, and don’t talk about it.

    Ok, well…this blog post is getting long, and I’ve covered a lot of ground. Also, I’m kind of hungry. So, forgive me, but I’m going to post it as is, and answer more later. Feel free to comment below with thoughts you’d like to contribute and/or any advice you have!

    9 thoughts on “Etiquette 101: On a Date with an Escort – What to wear, grooming, conversation, money

    1. Also nice to have some small items near the envelope such as favorite chocolates (Cadbury, I believe) and a bottle of (unopened) wine to share. Little things you pick up by reading the provider’s webpage and showing a bit of thought and whimsy.

      1. I love this idea! What a great way to start the session. I can’t speak for other ladies, but chocolates will get you on my good side immediately, LOL. And yeah, it’s especially sweet when they bring something you’ve mentioned enjoying, even if it’s something little. It’s a nice touch that shows that you specifically chose to meet with her–you’re acknowledging that she’s an individual, not interchangeable with any and all of the other providers in town.

    2. I suggest than the client offer to provide refreshments . A simple “What do you like to drink?” is the best way to approach this. The usual answer is some type of wine. My tip is that you bring a corkscrew and appropriate stemware. It takes something away from the experience if you drink a nice wine from hotel room plastic cups.
      Jim

    3. I’ve definitely enjoyed reading your Blog and Q&A. I’m a firm believer in proper grooming. I know you ladies put in the effort to look good, it’s only fair us guys aren’t showing up with 5 feet of nose hair or long gross toenails.

      1. LOL agreed.

        Actually, that reminds me: if you want to finger-fuck a lady, make sure your fingernails are immaculate–clean, no hangnails, trimmed fingernails, no sharp edges. I know some people work with their hands and therefore simply won’t be able to meet these standards, and I respect that. But if you fit that description, please respect that finger-fucking is off the table for you.

        1. Manicures and pedicures have become a standard part of my grooming just like shaving and haircuts. I love what my courtesan has taught me. Now she just needs to read my text messages lmao
          Jim from Nashville

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