Anyone ever dated women much wealthier than you? What's the biggest free-money women have given men?

[CountSuavula]

Yep, it's happen a few times. The GF also pays for a lot; at her insistence. We earn about the same salary wise. I've dated doctors and lawyers; a lot of money; but pains in the a$$. They also have big egos for some reason; not sure why.

I have not been romantic with any old money women to my knowledge. But I have friends with it.

There’s a difference between a women who is a doctor type of working stiff and a women who’s family name is on the city center buildings from hundreds of years ago. So there are different levels.

At the end of the day people with old money like that are a bit different. Some of the most exceptional friends I have met in my life are from old money backgrounds. There are differences in the foundation of lifestyle.

My family is not old money like that but I do have similar generous mannerisms about life and with people.

 

[CAPSLOCK BANDIT]

I've done it, the problem is that you don't have an active position to manoeuvre from, your only position is to physically not be there... For me as a example, I leveraged my time into being a father figure for her son, not because I like the kid but because I want her to see him go without that when I don't get what I want.

To actually have this relationship with somebody in a healthy way, you need to communicate all the time... Like she asked me if I wanted to have sex one day, I said no, I just didn't feel like it, so the plumber comes over and she literally invited him upstairs into her room while I was downstairs and banged him, I had no idea, there was another guy she had me texting on her phone to stop texting her because he said her loved her, turns out she picked him up from a tim hortons in her giant souped up truck and he creampied her in like 10 minutes of knowing her.

This is the type of things that can happen when you have communication issues when your dating a rich woman, they move quickly, you need to stay in the pocket and deal with issues maturely and quickly, she needs to respect you.

By the way, this is all without the use of Online Dating, you take that into account it's just another thing entirely

 

[Millard Fillmore]

If I could go back to my 20s I'd be more of a gigolo - not all the time, but living in NYC I definitely could have paid some rent. I was a piece of a$$.