It's something I'd like to find out more about. Inspired by this piece on old school playboys (
http://takimag.com/article/when_gigolos_were_he_men ) I swung by Bemelman's at the Carlyle in NYC on a Friday night hoping to find some hot, wealthy divorcees.
Crowd was mixed. All 30+ and mostly over 40. A lot of couples on dates. Men are suited up and women look glamorous. There were some cougars there by themselves. Speaking to them I mostly got a gold digging vibe, though.
Cocktails were $20 and there's a $15 cover to sit at the bar. Cover is $35 to sit at a table. There's live jazz on most nights and a very subdued, old school vibe. Would be a perfect date spot if prices were lower.
It's almost all sit-down, though more and more people were standing by the time I left at 11pm. Racking up approaches is tough because of this. There's a small bar where you can sit and chat up whatever comes your way. Right before I left a forty something blonde I was chatting to by the bar invited me to sit at her table. She wasn't all that attractive so I declined and went to see a couple of young prospects downtown.
I wonder where else should be explored in NYC for this? I'll keep at it and can write up a sheet in a couple of weeks if there's any interest.
I'm not going to do it for the money or lower my standards, but if there's a hot divorcee who wants to open some doors and take care of me I'd be cool with that.
Related question: How do you get girls to buy you things? I know one player who got his (young, hot) girlfriends to give him stuff all the time. He talked about things he'd like to have, they'd get the hint and buy him presents. I've heard similar stories from friends who have dated wealthy Saudi girls.