Should you date a Richer Gal as a Young Man?

Men have fears, concerns, and esteem issues when it comes to dating. What are some of the reasons men don’t want to date a rich gal;

  • She might henpeck you
  • You might be her dress-up doll
  • You might be her ‘project’ she is trying to make successful
  • Her family might look down on you
  • Her friends might not like your ghetto ass
  • She might lowkey feel like you are not on her level or the best she can get. She might later ditch you when she feels like she compromised to date you

This list is endless. There are tons of reasons men fear gals who are wealthier than them, are from rich families, or have better jobs.

First of all the world doesn’t work like that. A rich young gal dating a middle-class guy or a lower middle-class cat is a recipe for a potential disaster. I have been fortunate to be around young men who are actively dating and time and again a few of my friends have found themselves in relationships with gals who are richer than them. I mean gals not older women looking for toy boys.

Whenever any of my friends tried dating a gal richer than them, they came back a shell of their former selves. Their frames broken, their esteem lowered and their masculinity and sense of self-worth shaken a bit.

One crucial thing men from the middle class like me or the lower middle class feel about rich gals is that they are entitled and rather bossy. Entitlement is a thing you will also find in hood rats not only rich gals.

A rich gal might be used to being given everything and not told no her entire life. She might be having hordes of orbiters around her who do anything she wants them to do. When you come into her life and try to enforce the pimp’s hand, it doesn’t sit well with her and thus ensues the frame battle.

If she is the one paying most of the bills in the relationship, you don’t have the financial muscle and the commanding voice to be the leader in the relationship. One friend of mine on campus who always dated rich gals who would pay his rent and take care of him would constantly complain about how bossy and controlling the gals would be sometimes. This is because he yielded his frame to the gals some of the time. He had to constantly nag the gals and pester them for favors he needed from the gals. Dude was a hustler.

The situation would have been different if he just held his own, had his things, and didn’t need a gal’s money. You can be the middle-class guy with a strong frame who pays his bills and takes care of himself dating a rich gal, the problems will not be many but they will still be there.

Another friend of mine who has a very good game and is masculine tried to date a rich gal three years older than him who owned a spa and drove a luxurious car and he ended up being policed like a child. He couldn’t even talk to us in our group or join us for a boys’ night because the gal was monitoring his messages. Mate guarding him like crazy. He too was driving the lady’s car despite having his ride and probably receiving a bit of funding from her. That sounds like a good deal but his freedom was gone outside with the wind. It is not the first time this brother tried dating out of his league. He tried dating a rich gal when he was younger and things went rough for him despite the gal being the one who approached him on social media. This brother also comes from a somehow well-off background but he tried punching above his weight a few times and got burned. He came back a shell of a man.

You might think my friends mentioned in the above scenarios would have just stayed on their level and not started using the gal’s money or driving their cars and things would all be merry but it doesn’t always work like that. If you are dating someone you won’t avoid the financial aspect for long. At some point, you will go on a trip with this person or you will go out for a dinner or a group activity or you will live together.

When you do these couple activities for bonding, don’t start to think she will downgrade to make you feel comfortable in your mettle as a man. She will bring up the money issue every time in an argument and how you are broke whenever there is a problem that doesn’t even have to deal with money. Women know men are sensitive about their money or masculinity and will try to use it as a tool to cause problems and hit their ego. If you doubt yourself and start explaining yourself, you are dead meat. In such cases, you can put on a straight face and claim that your value as a man is immaterial. It might work for a minute.

Let rich people date fellow rich people. If you want to date a rich gal, one of the best ways to do it is to also become rich. Every societal group has a mindset or a mental model they live by and when you are a hustler, your mental model is different from that of a trust fund baby. Your mental models might clash all the time. You see things very differently.

she might not find his hood jokes funny!

One of the easiest ways to understand this as a young man is to befriend a  kid who is from a very wealthy family. You might not be able to relate and relatability is an important factor in dating. Attitude similarity between people goes a long way in bonding and pairing. In the same way, if you are a middle-class dude and try dating a ghetto chic living check to check, you will have a hard time understanding her mindset.

There is one trick in all these, if you are a social chameleon, a guy who is very socially savvy and can mix up with different groups of people easily and get along with them, you can maybe date from a different class and make it work out. It is hard but you can pull it off. However, the class difference can’t be so big. An upper-middle-class gal can date a wealthy guy and make it work. However, the same upper-middle-class gal might have a problem with a lower-middle-class guy still trying to find his footing and put his shit together.

Hookups happen among people from different classes. That sexy dancer shaking her behind can shag an investment banker because she is attractive. The sexy male stripper with charisma and good rhythm who is confident in social situations can shag a trust fund lady but might not be able to date her. The difference in education and social status is a barrier.

The family of that rich gal will look at you funnily when she tries to take you home to meet Mom and Pop. She might be a rebellious rich daughter bringing bad boys home. There is a perfect movie that displays this called ‘Peeples’. I watched it many moons ago and I liked it though it is pretty average. Check it out sometime.

Don’t think for a second that a rich girlfriend will help you skip the line, well she might but where’s your position in the house? You will automatically be slotted in a subservient position. I was listening to a podcast where a guy said that he once dated a rich girlfriend from a rich family and the gal told him one day that if they were to get married, her dad would buy them a mansion. The guy was adamant, he ignored all the promises of fortune, and many years later after breaking up with his girlfriend he’s been able to work his ass off and buy himself a mansion.

Rich gals also have a few advantages, don’t ignore them because they can be entitled and snobbish or soft or dramatic. A rich gal can be very classy, she will wear designer colognes and look so fresh when she steps out with you. Another pro is that she is somehow independent and won’t need your cash, she can pay for her Uber or drinks or rent or anything she needs. She won’t hustle you, unlike a gal who might need you for her upkeep. It is up to you to decide whether the pros of dating a rich gal outweigh the cons or the other way.

Are these concerns genuine or based on insecurity and low self-esteem?

Experience is still the best teacher. If you think you can get that rich gal. well, I won’t stop you brother, take your shot but be prepared for heaps of drama. She will be worried that her friends are dating multimillionaires in real estate and investment portfolio managers and here she is with a customer care assistant manager at a no-name corporation. If you can handle the drama and remain strong and unfazed despite the chaos, go for it.

Most of the time men can’t deal with a spoilt rich girlfriend and their demands. Whatever I have written is from experience, not armchair psychology.

Break a leg!


By Slade Jeff

I am a zen, I love this life plus a lot of wine..I will keep your days filled with interesting content. I am also pro-brands, I tell stories about them at a fair price, let me put in a good word for you. Contact me through for business.

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