What to do when dating a high value man who is financially struggling 

Hello, Gorgeous!

Have you ever met a gentleman who is a true provider but is not financially where he wants to be? 

The kind of man who 

• always shows up when you need and want him 
• has the good character of a prince you read about in fairy tales 
• loves you endlessly  

Technically speaking, he is ready to settle down with you and sees your futures intertwining but is still building himself. This is a provider and we are trying to find these good men.

They are everywhere and they all start somewhere.

There are 2 schools of thought when it comes to a successful relationship.

I used to listen to a lot of podcasts pushing the traditional approach to dating long ago but stopped because I found my sweetheart. My experiences in relationships include all of the ones mentioned below.

The first philosophy

You grow together, because you are both young and have big plans. You either have your lives together or are working on everything together as a team and want to grow concurrently. You are mostly equal across every aspect of life. 

The second approach

One is already fiscally stable whilst the other is still figuring out their pecuniary duties. The more economically successful one is either guiding or carrying the other yet sees them as an equal partner in emotional commitment.  

Don’t forget balance.

Sometimes one or the other occurs in a relationship and roles switch. Circumstances alter when finding a new job, moving to a new place, or health predicaments change. All of these cases happen in all phases of life and are normal. 

Provider types: Is he a drain or is he a daddy?

If you are here, I highly suspect you are a traditional woman seeking either a hypergamous lifestyle or your true counterpart. Meaning you want to date your equal or better to improve your own life. 

There are countless studies that found women tend to date equal or up whilst men date equal or down. The study covered all facets of life–not only monetary obligations. 

Here are concepts to consider.

Evaluate His Values

Being a provider does not automatically include being rich. 

Wealth isn’t the only marker of value. Look for integrity, ambition, kindness, and consistency. He is chalant.

A provider typically is 

• looking out for your interests
• has a good, generous heart in general 
• does everything he can to make sure you are not missing anything

The provider gentleman inspires growth, respects you and your boundaries, and does not feel uncomfortable handling challenges. He is a good man and values you. 

Separate Financial Status from Character

Being fiscally challenged doesn’t mean he’s less than. Focus on his mindset, goals, and how he treats others. 

I have encountered a handful of rich people ($50,000 a day earners) who were the stingiest penny pinching misers I ever met in my life. 

They had demanding attitudes and were impossible to be around, because they needed the attention level of a newborn baby. But they were old, unattractive, and rude. 

Money does not determine if someone is generous and compassionate.

Some people want to be comfortable and others want to rule the world. Both ideas can apply to healthy, normal individuals who want loving, healthy, lasting relationships. 

Check if he is working toward financial stability or content with complacency.

How to spot ambition and potential

Is he trying to make fetch happen? 

There are drains who have dreams with no deadlines. Spotting them is easy because they talk, talk, talk, talk, talk with no action. 

These idiots might take shape in living off of their parents into their 30s having never flown from the nest. Or come home after an 8 hour shift to play video games for 5 hours straight with a side of smoking weed. Or does nothing with his time that shapes his future at all outside of work. 

We avoid this human altogether, because we cannot relate as It Girls.

Nepo babies to consider: The daddy’s boys

There are 2 main archetypes. Obviously, there are more nuanced classes of them, but we are sticking with these genres today to keep it simple. 

If someone is already financially successful, the proof is not always in the pudding. He could have inherited his wealth and sits on his bum all day. Or he learnt from daddy, because he has great relationships all around.  

The grown up daddy’s boy

This is an interesting fellow who is usually a charming silver tongue who always gets what he wants yet still knows about hard work, because his father taught him. It is not necessary for him to do hard work, but at least know about it in depth and/or theoretically.

He never has to deploy these senses because he is extremely wealthy. However, he can hold his own in a room of private equity general partners and crypto bros. 

He knows so much, because he is either going to take over daddy’s legacy one day or create his own enterprise. 

Most likely, he went to a great university and holds pride in his education and upbringing. 

Money is in his bloodline and success – whether it is his own or not – is also a genuine interest.

The mandchild daddy’s boy

A woman I knew had a long term on and off relationship with a trust fund manchild who was in his 50s that was on the verge of being cut off, because he never worked. His octogenarian parents were tired of him asking for an allowance and were sick of his entitlement. 

Sometimes they start as the grown up daddy’s boy, but something happens such as a physical injury, or he never grows out of the playboy stage to settle down for a family. 

The daddy’s boy I am more familiar with is the first type, because several exist in my friend groups. 

The self-made man

We like this guy. 

If he is self-made, then the ambition is there. In other words, if he lost it all he can do it all over again faster, because he knows exactly what not to do. 

Also, he knows how to talk to people and make everyone feel comfortable, because he knows how to get what he wants or communicate his point seamlessly.

He is most likely the one whose current bank account isn’t as important as his drive, skills, and ability to grow. This knight in shining armour is either on his way to financial success or already achieved it. 

It is also more possible he is down to earth because he generated his own success by knowing the ins and outs of working hard and smart all on his own. He figured out the key to his success. 

You can trust him to take initiative, solve problems, and plan for the future.

The self-made man is always a green flag, but the daddy’s boy might need some vetting if he is not already a playboy who has a new model girlfriend every time you see him.

How to navigate dating a high value man who is financially struggling

He was worth the wait. Is he worth keeping in your life? 

I cannot decide for you, but I can help guide you through this scenario. It is probable that you have encountered a provider in one fashion or another. They all start somewhere. 

Set Your Own Boundaries

Be honest with yourself about your financial expectations in a relationship.

Decide what is non-negotiable (e.g., lifestyle compatibility, shared responsibilities) vs. what can be flexible or is fixable.

Sit down and speak from your heart to the potential love of your life. You are most likely attracted to this guy and want to hang onto him. 

Find out if you are on the same track.

You want both of you to be successful no matter what. That is what a good relationship does to people. A healthy relationship is 2 people showing up at their best for each other.

Good lovers set the bar high, because they know the other is beautiful in every way and want to have no competition. Being able to sleep at night knowing you showed up as your best is a good thing. 

Assess whether he will have it all one day as the total package by considering the aforementioned concepts to consider. This is terribly imperative as an It Girl, because you are always working on yourself especially if you want a family one day. 

You want the best for your children and that includes a loving father who can sustain them through the roller coaster of life. 

Choosing your partner is one of the most significant decisions you will ever make in your lifetime and literally changes your entire bloodline. 

Emotions and logic might not always match, so find out early to know if you need to walk away. 

You are not a golddigger because you want your children to go to exceptional schools. 

A rich man wants the mother of his children to have a house that is similar to his after a divorce, because the sudden shift in lifestyle when she moves to a sad apartment will make his own children hate him for making their mother suffer. 

Seeing the drastic two differences of lifestyles will mess with their heads. 

Your partnership affects absolutely everyone and everything.

Focus on Mutual Growth

High-value relationships thrive when both partners challenge and support each other, not only financially but emotionally and intellectually. 

In divorce court, when a man has a ton of assets, it is still difficult to divide, because even if the wife makes less, she offers so much in unpaid labour and emotional support. 

Encourage shared goals, learning, and experiences that build connection beyond money. 

Whether you can sit down for hours yapping with this wonderful person or sit in silence the entire night exchanging affectionate glances, you want to be on the same page working towards the same goals. 

This could entail purchasing a house one day, having a family, and/or building a legacy together.

My ex-husband and I were not on the same page financially, but he taught me a lot and we both walked away having learnt each other’s strengths.

He made a great point of having weekly expenditure meetings to realise our spending, growth and what we could work on. Fiscal awareness together makes an elegant marriage. 

Decide With Clarity

After observing values, ambition, and character, decide if this man fits your long-term vision.

DO NOT settle out of guilt, pity, or fleeting attraction. True high-value connections are aligned in vision and integrity, not simply fiscal triumph. 

The love of your life might want you to have the moon, but no rocketship for your pretty peach to sit in. Whether he has a rocket or not. 

A man’s worth isn’t measured in dollars—it’s in how he shows up, respects you, and builds a life with you. 

Set your standards, watch his ambition, and don’t settle. Your love story deserves a king, not a wallet.

A real provider shows up, supports you, and inspires growth. Cash is simply the icing. Evaluate, observe, and decide with clarity. You are not here for pity, you are here for true partnership.

Know your worth. Anything less isn’t the vibe. 

Any changes are to be made in writing. You’re welcome. 

Level up your life, love, and legacy. The It Girl School shows you how to stop chasing and start attracting what you deserve.