Dating like a Pro

And now, for something completely different.

I’m proud to host Putanumonit’s first ever guest post, by my friend Charlie Sun (not her real name). It’s on a very interesting topic, certainly one that I couldn’t write about myself.


The setting: a weekday evening in a fashionable Manhattan restaurant.

Me: Mid-20s, attractive, bored and restless at my corporate job. Want to make some additional income, but don’t want to be a waitress/bartender because of the physical exertion and the meager pay per hour.

Him: Mid-40s, a wealthy businessman, married or divorced, workaholic. Wants an evening with an attractive young woman who can make him laugh and give his mind a break from the responsibilities of his demanding life for 2 hours.

The fee: $200.

He has the roasted beets with fennel and almonds. I have the fresh squid with fava beans and asparagus tabbouleh. Then comes the rack of lamb with truffle oil French fries and grilled lobster with a side of filet mignon. If there are oysters on the half-shell, I order some – I always come to those dates hungry. Dessert is chocolate soufflé. No alcohol – I don’t drink.

The bill: $250, at least.

Conversation goes as normal conversations usually go on dates.

Where are you from?
What do you do for a living? (I keep this brief since clients are usually trying to escape thinking about work.)
What do you like to do for fun?
Where have you traveled to?
I never ask about family life unless the client brings it up first.

Be charming, flirtatious, classy and interesting. Make him feel interesting, understood and most importantly, relaxed. Be company worth paying for.

Some people clean toilets for money. Some analyze spreadsheets all day. Some perform complex surgeries. I got paid to date. Those are all jobs that need doing.

If you’re wondering if I had sex with my clients, the answer is no. I have never felt attracted enough to any of them and I was never desperate for money, making $70,000 per year at my day job.

I admit that I’ve been tempted to sell my body in addition to my looks and personality. A divorced lawyer from D.C. offered me a $6,000 monthly allowance in exchange for 3 full nights with me every month. The money would be in the form of a debit card, not in a shoebox of Benjamins if that’s what you’re wondering. I politely refused because he looked like the dark-haired version of Donald Trump.

An Indian tech entrepreneur offered me as much as $8,000 per month in addition to international weekend getaways. I refused him as well because even though he was very charming and funny, I just couldn’t stomach the image of being naked and sweaty with him.

There were many more and honestly, I would’ve gladly accepted if I had felt any physical attraction. I refused them the same way that I would refuse any man I didn’t want, and for the same reason.

I did have a regular client who I saw for a year. He was divorced, had a daughter my age and owned a startup. When he found out that I loved Broadway shows, he began to take me to any show of my choosing once a month. Except for Hamilton, unfortunately, although he did try. Fancy dinners before the show, and a $300 fee for my company, always sealed in a beautiful envelope. I asked him for advice about my problems with work and family. He told me about his experience with marriage, divorce and raising children. I didn’t need him and he didn’t need me, but the exchange was fair and agreed. Did he want to sleep with me? Of course. But he was a respectful gentleman who appreciated my company and didn’t want to make me uncomfortable.

They haven’t all been rich. I once chatted with a Verizon technician who just came from the picket line. We talked about our lives over chips and guacamole in a lower east side bar and I went home with a hundred-dollar bill.

There have been real estate tycoons, bosses from the oil industry, doctors, film directors, restaurateurs and many others. All had the same things in common: they were busy beyond belief, they had money to spend, and they wanted a night out in pleasant and attractive company. Many were also in turning points in their lives, as was I. It was lovely to compare notes over seared ahi tuna, and to pocket the cash afterward.

I’ve only met 2 other women in my line of work. One was a 20-year old waitress-turned-English-teacher whom I met in Barcelona, and she actually slept with clients for $500-$600. Too cheap in my opinion, but to each her own.

The other was a 27-year old aspiring Broadway actress who was a banker’s mistress with a $5,000 monthly allowance. I was extremely jealous of her jackpot arrangement, and apparently, the client was a total sweetheart. I guess by the time I stepped onto the scene all the men worth sleeping with were taken.

I asked a few clients about their experiences with other escorts. I was surprised to hear that many girls showed up on dates looking unkempt, could not hold a conversation, and didn’t have much direction in life. What most clients liked about me was that I was always pleasant company, had a solid career of my own, had a multitude of hobbies, was well-traveled, and could make them laugh. I guess I just took my job more seriously than others.

One client told me an escort’s photo showed her with blonde hair and she came to the date with pink hair and a face full of piercings. He was horrified at her dishonest advertising but still paid her for her time. Another client recalled a pleasant evening with a beautiful Swedish escort but at the end of the date she said, “I have to go now, can you pay me?” How indelicate!

No client wants to feel like he’s paying for company, even if that’s what’s happening. I believe most of my success was due to my professionalism and understanding what the client wants. I never showed up rolling my eyes or with my hair uncombed, to my day job or my evening job.

I hope there are some female readers out there who are becoming interested in giving escorting a try. Just do me a favor and do it intelligently, like readers of Putanumonit should. Let me tell you the details of getting clients.

Like any other service, escorting can be found online (duh). The websites are designed almost identically to OkCupid or, only asking for a fee in exchange for a date is expected. (OkCupid is where I met Jacob, so I never made him pay extra to hang out with me.)

Put up some attractive but classy photos of yourself. If you look like class, you’ll attract class. If you look like trash… you get the idea. In my profile, I wrote what I genuinely liked to do; reading Emile Zola novels, eating dark chocolate, hiking in the mountains, cooking stir-fry dishes, etc. There was no need to be dishonest here, I wanted to sell my real personality to attract someone.

Then, I’d scan the list of men for anyone I could be interested in. If there was, then I’d write them a message simply saying hello and that I’d like to meet them sometime. I was rather passive at the start since it was the men who were doing the actual purchasing, but it’s nice to be proactive. Men would write me a message to introduce themselves, complimenting my smile and asking for my availability. And the most important thing is, negotiating the offer. I would usually ask for $200 and if that was too much, we’d negotiate down to $150. Any less than $100 isn’t worth your time if you’re going to do this, ladies. Sometimes a cheeky guy would offer $99 but when push came to shove, he still gave me a $100 bill and didn’t ask for change.

If the messages are polite and gentlemanly, I accepted. If they seemed to be solely interested in sex, I refused since that’s not what I’m selling and they’ll probably make me uncomfortable anyway. Then I would pick a meeting place, and I wasn’t shy about it. I made a list of the most luxurious restaurants and cafes in Manhattan and I checked them off one by one. This is your opportunity to be extravagant but remember: the client is interested in you, not the restaurant.

Then, you deliver. When the date is over and it’s time to receive your fee, just politely ask, “Shall we settle?” Do NOT say, “Can you pay me?” Don’t worry, they always give you your fee, at least in my experience. Sometimes a client will offer to drive me home, which I’ve accepted many times because I felt comfortable with them. If you don’t feel comfortable then have them call you an Uber. Being driven home in a Porsche isn’t too bad either. Remember that these are busy men.

I’ve had many incidents when the client cancelled at the last minute because he had an important conference call or had to jet off to another country. Don’t be sour about it, he’ll see you when he gets back.

When I told my close friends, I was pleasantly surprised at how supportive they were. One female friend was against it because she thought prostitutes were addicted to drugs and were constantly beaten up or strangled in an alley. How very Hollywood. That might be true in some cases, but it definitely wasn’t close to the queenly treatment that I received on the job. I made more money than all of my female friends at that time, and they all knew me as someone who did exactly what she wanted who made all decisions deliberately. Most were mainly concerned for my safety, understandably.

Nearly all of my male friends wished they could be a part time escort too, if there was a decent market. I did notice how men would openly joke about it, and women would raise their eyebrows, smile and edit their thoughts before saying them to my face. I honestly don’t care what they were really thinking. When I would recall an evening out, I could sense many people living vicariously through my adventures (and what I ate for dinner). I enjoyed that. It’s a wonderful feeling to do something that most people are afraid or ashamed to do, and see their envy once you do it. After all, I wasn’t searching for my true love here.

If you’re concerned for my conscience, don’t be. I highly doubt that I ruined any marriages. In fact, most clients valued discretion more for the sake of their professional life than their married life. They didn’t speak much about their wives but when they did, it was always the same reason. “I’m staying for the kids.”

Sounds familiar? One Italian importer/exporter simply said that he loved his daughter and he had a great house. He revealed that he and his wife had sex 3 times in the last year, all under the influence of alcohol. He even hoped that she was sleeping with another man so it would make her a nicer person to be around. I hope it wasn’t this bad for all of my married clients but none ever seemed to feel guilty in my presence. I never felt guilty either but I did wonder how the wives would feel if they knew what their husbands were doing.

Would it be too blunt to say it wasn’t my problem? Supply and demand have no feelings, and this was my job. I never lost sleep over it. But, it did make me wonder about the boyfriends of my female friends. As the years went by and the excitement slowly faded, would they also hire escorts and hide it from their wives? What life events or personal qualities led a man down this path? I still don’t know.

But if I do it, then what does that say about me? I’d be a woman of loose morals. No man would want to be with me after this.

That sounds like all we’ve done is to trade an old set of patriarchal rules for another, and women’s behavior is still dictated even in this modern-day feminist extravaganza. Fuck it. Do what you want. It’s way cooler, trust me. And you’d be surprised at how many guys like me more for how unconventional I am.

I really wish more women (and men) would use their sexuality. Not in the sense of “how can I look more like a Victoria’s Secret supermodel.” That’s too superficial, unless you actually aspire to be a Victoria’s Secret supermodel. I’m saying: use it intelligently. There’s nothing wrong with using your looks, but you must consider what else you’re bringing to the table to complement them. What do people actually like about you? What image are you creating when you speak? How do you increase your value in their eyes? How can you get someone to open up? What qualities do you naturally possess that draw people towards you?

Enhance those qualities to draw in the right people who could change your life. There’s always an audience, and knowing how to seduce it will open more doors than you could possibly imagine.

Many feminists would probably skewer me for doing what I did, but I stand firmly by my decisions. It’s exciting to do something so socially taboo and enjoy it as thoroughly as I did. I had a fucking blast! I met people whom I’d never imagine being able to meet otherwise. I got career and financial advice from some of the most wealthy and powerful men in New York. I got to know, in detail, all the different problems that could arise in a marriage gone sour.

I dined in luxurious restaurants and ordered anything I wanted. On more than one occasion, I ordered 2 entrees because I had the appetite and wanted to try everything. If you’ve never done this before, you have no idea how fun it is.

I made money. Cold hard untaxed cash. Sometimes a wad of twenty-dollar bills snuck to me under the table and sometimes folded neatly and presented in a beautiful card. I made a whole month’s rent once, just from eating in a fancy restaurant and being a charming date.

I’m a schoolteacher now, which is way harder than escorting. But being a freelance escort was great practice. I learned some invaluable skills in my two years of doing this:

How to keep conversation going, no matter what.
How to make someone feel like an interesting person even though he/she is a complete bore.
How to build a connection with anybody in 30 minutes.
How to steer conversations when they’re getting too personal or making me feel uncomfortable.
How to ask for exactly what you want and not be shy about it. Like ordering 4 desserts at a 5-star restaurant, because I want to.

How many corporate cubicle jobs allow you to build these skills? I got tons of practice and instant feedback. I use these skills almost every day to connect with new people. I get more of what I want because I have the balls to ask for it. This kind of job obviously has a shelf life but I’ve retired with a wealth of experiences, not just money.

Some people called me a sexy therapist. Some called me a whore.

Call me what you want, I had an excellent time.

16 thoughts on “Dating like a Pro

  1. smiley

    I enjoyed the read, can we expect guest posts to be a regular thing in the future? (albeit in that case, I assume you’d have to spread them out or something, to keep putanumonit putanumonit)


    1. The frequency of guest posts depends mostly on the guests :)

      While there a few core ideas behind almost everything I write, Putanumonit (as you surely have noticed) ranges over quite a wide range of topics. My primary goal is to write and publish things that I personally would enjoy reading, as was the case with this story. Anyone can send me an essay, if it’s something I enjoy reading I’ll edit and post it.

      I did spend 3-4 hours editing this essay and sending drafts back and forth, it’s still easier than 8-10 hours of writing.


  2. I’ve been a big fan of your blog, but this was an off-putting post. Little more than bragging and self-justification by someone who seemingly never matured too far, or never had to spend much time thinking. I seriously wonder if this this guest post was some sort of hidden, second level men’s rights signaling. I don’t even know why I wrote this comment since I doubt this helps anyone. I’m sorry. Maybe others who felt like they could trust you not to waste their time will relate.


    1. How would this post be men’s rights signalling? The only sentence that implied that to me was when she said feminists would skewer her for it, would just showed me she was very well informed about the feminist movement.


  3. I enjoyed this piece, but it didn’t really feel like putanumonit as currently written. For example, I’d love to hear about how you (the post author) feels about your rate. I’d be curious also to know if you have kept any logs and recorded anything which can be mined for interesting trends in your own behavior, and noticeable changes in your attitudes towards people, social settings, your own relationships, etc. Thanks =)

    Liked by 1 person

  4. My only remark is that you should have declared the income and paid tax on it. This holds in a moral sense; you were able to do the work you did because you felt safe doing it, and that safety ultimately relies on the existence of criminal sanction for misconduct and by not paying taxes you did not contribute your share of paying for the system. It also holds in a practical sense; in terms of the risks you take, there is a big difference between having something potentially embarrassing in your past, and having something criminal in your past. Within a five year window, I believe you should be able to file an amended tax return (note: I am not a tax professional and nothing I say is tax advice).


    1. Great article, but FWIW, I also think that people who earn cash should pay taxes, so I’d ask that people in this position give it some thought.

      I know – everybody has better uses for the money, but I’d still rather live in a world where people pay their taxes voluntarily, and a few radical anarchists aside, most of the rest of us probably do too.


    1. That’s why this post is tagged both “love” and “capitalism”, two subjects that Charlie and I learned a lot about from each other. You caught a good point that I didn’t think of explicitly as it relates to the story: if two people are engaged in a voluntary exchange, and neither of them thinks that they’re being exploited, I tend to take their word on it rather than listen to outsiders.


  5. I enjoyed this post. I’ve read some similar things in the past. It just leaves me wondering what’s going on with the market since $200 dollars an hour sounds like altogether far too much for some pleasant conversation. Is it just that it’s a new-ish industry and it’ll take some more time for the prices to reach equilibrium, or is there some reason I’m not understanding why more women aren’t doing this?


  6. This individual can to what they want with their time. It is great that she is attractive enough to elicit that kind of fee. Well, if there is a demand then there will be a supply. However, it does turn my stomach a bit to read it. At least this was an explicit transaction, verse, articles I have read about women professionally dating with suitors looking for a relationship. They just did it for the food in NYC. It was done so professionally, they the individuals kept spreadsheets. Now that is down right terrible.
    Overall, I think her post shows how awful dating and relations between men and woman have become.


  7. A guest post offering a window into the world of transactional dating.

    I was half-expecting this post to be about the kind of dating where if a date goes wrong, the entire date gets rolled back and your relationship doesn’t end up in an awkward invalid state…

    Liked by 1 person

    1. I actually do this sometimes while messaging on OkCupid. I will literally point out if the messaging is going down some boring alley with increasing gaps between responses, and suggest a restart on a new topic.


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