1. No matter how rich (up to the b word), some men control every dollar (and you, by extension).

Some men use money to control, others use it as a resource. When I was more naive, I learned some harsh lessons about the way some men relate to their wealth. If they start offering you extravagant things that you never would have asked for, or they assume that you’re only there for money (because that’s how they approach life), tread carefully, as they’re probably negotiating the best deal (at your expense).

       Dealing with men like this can be interesting, but ultimately, you’re speculating on futures in a rigged market. 

       Since then, I’ve met some wonderful, truly generous men and understood that to them, giving is part of what makes their success meaningful. These days, I’m much more impressed by good character than his net worth or the number of cars in his collection. 

2. Generally speaking, the more successful, the more intellectually humble and openminded. 

       I expected very successful men to be arrogant and possibly boring, but instead I found them to be some of the most openminded, knowledgeable and interesting conversationalists. 

       The combination of holding strong opinions and seeking to learn from others is rare and exciting to encounter. I was also flattered by their curiosity in my views and willingness to be influenced by my perspective.

       These conversations opened my mind to new ways of seeing the world. The advice I received has been weightier than gold and I think about these conversations often (I am lucky to remember good conversations word for word, for a while).

      I have not found this unique approach in men who are in middle-ranking positions, even in those same fields.

As an aside, alongside this unique way of thinking, the rituals and habits of the most successful men I have dated are often similarly singular and unusual. As people, they are often endearingly odd. Luckily for them, cute and nerdy is just my type. And I am also quite odd myself. Endearingly, I hope.

3. My obscure humanities education has finally paid off.

       Who knew that this would be how I'd cash in on my classical education? Not me.

Rich men love that I know Greek and Latin and that I have studied in obscure places. In reality, these were incredibly impractical life decisions (e.g. hopping on a plane, praying that my scholarship money would come through before I landed).

      I never really cared that I was not working towards a lucrative or even certain career path, I had no tolerance for boredom and I just wanted to learn what I love.

       Now that my prefrontal cortex has developed, I do like money and building financial stability a whole lot more. That said, I really love the growing collection of gifted Loeb classics on my shelf. Please don't stop.

4. Honesty over platitudes. 

       I have pleaser tendencies (both the good and the detrimental type).  Being around people who spoke directly, respectfully and concisely demanded the same from me (especially when money was on the line, we adapt fast).

       I was excited by this way of communicating, and used it as a way to learn to drop the performance and be direct, kind and self-respecting instead.

      This made me a whole lot more trustworthy, too. And perhaps more money as a result, but to me, this skill is valuable beyond financial measure.

5. Yes, it's true: if he’s the top dog at work, he’s probably a bit submissive in bed (and I love that).

       Well, it can go either way.

I would never share personal details of clients (and other providers shouldn’t either), but I will say this: life is all about balance.             

      When our environments demand that we present only one part of ourselves, the other suppressed parts surface in interesting ways.

       Pressure needs a release valve. Some people go to Sorrento, others half drown themselves between the thighs of a beautiful woman. Personally, I enjoy both.