Hmmm, very interesting. In college, between the ages of 19 and 21 I worked at a pizza joint some summers to support my drinking habits, and hung around with the owners and some of their much richer restaurateur friends. Incidentally, I was very surprised to see how many of these very charming and funny, older, and utterly uneducated restaurant owners were in fact millionaires many times over. All these characters, some married and some not, were after the ladies and they would tell me, in a Marlon Brando sounding voice:

'David, if you ever want to get into the sugar business you really need to stop wearing jeans and instead exude power, affluence, and liberal spending habits. After all that's what women want', said my Cadillac driving and pinky ring wearing acquaintances. And these guys would be hanging out with some very attractive 20 year old college students, and pulling out some very thick rolls of $20's and $50's.
Whatever happened to women wanting nice guys with personality and education? Anyway, out of all those habits, the only one I picked up is the rolls of $20's and $50's, and some times talking like Marlon Brando, lol. Never liked Italian suits or pinky rings. Prefer custom made business suits, although I don't wear those on sugar dates, generally. Prefer to be a bit more casual. And luckily many trading floors also have casual attire. By contrast to, say, law firms, or management consulting companies.

Jesse

Was at work today, and walked around Midtown afterward. Passed by the St. Regis and this reminded me the first time I met my old 'pal' Jesse. We met outside the place, when the plans to meet at a sushi place of my choosing didn't work out. I am not a sushi fan but she was, and somehow I got stuck with picking the place. I wrapped up work one Thursday evening and then got a text from her saying 'Hey I know I am 30 minutes early, but I walked by the sushi place and it looks really bad'. Let's meet at the St. Regis instead, at the Adour. 'OK that sounds excellent' I said and proceeded to take the elevator down and started walking east at a fast pace. She said she was wearing a red dress, so she would be pretty easy to spot. In my mind I pictured a bright red dress, but in fact it was not, and we got all mixed up as several patrons had decided to wear the same color that night. We finally got it straight, thank God for text messages, as in: 'Look to your right, I am now waving to you'. She had a great dress on, that revealed just enough, and her entire length of the arms was showing. I asked her if she trained but she said she has done some manual labor in her house in San Fransisco for a while so she got into shape that way, and not body building. She was a recent transplant to NY and she was looking for a job here so I recommended some recruiters she could use.

Along with our light fare, the fist drink she ordered was a scotch, and I commented that is my favorite drink. I was somewhat disappointed though because she had it with soda and on the rocks (how clueless!). At least it wasn't single malt so not too much damage was done.
I noticed right away the tattoo across her bicep, written in Hebrew. It was something to remind her of her departed younger brother. I found that very touching. As the night wore on, she complained that most, if not all SD's she had met saw her as an escort. Of course I offered my sympathies since I know first hand the exact definition of these two very different situations. Conversation flowed very smoothly, and she used lots of hand gestures while she was talking. Maybe that's why got along. She was telling me about her hippie parents, and at fist, they gave her the name (I am not kidding!) 'Tree'. Then they wised up and named her Jessica, after the well known Allman Brothers instrumental.

After the first few drinks I switched to scotch. We both got so drunk, and I do remember walking down the street, and asking a lady what direction Bloomingdale's was.
We walked in about 30 minuted before they closed, and she found the sales consultant and announced to him in no uncertain terms that she was there to make some large purchases and needed his immediate attention. He complained he was only one person covering the entire floor but she wouldn't have it. I settled in one of their comfortable chairs and relaxed while she was playing around with my credit card. Don't remember too much other than we walked out with a few boxes of stuff, one of which as she said 'shows too much of my boobs'.
I got her a taxi, and then she did something that pissed me off: I leaned to give her a really quick peck good night, being a perfect gentleman, but she turned her head the other direction. What did she think? I was planning to slobber all over her? That was definitely a turn off. She turned out being just a friend and drinking buddy, and not much else.

She was one of the 2 women I know, that came out and said that 'In Europe, men are expected to have a mistress'. My jaw kinda dropped. How did she know? Well, she had lived in Italy and in Holland for a while. Cross cultural fertilization at its best...