Dating a Millionaire: 3 Big problems and how to solve them

Posted by | March 11, 2016 | Millionaire Dating | 4 Comments

Dating a millionaire isn’t always as dreamy as it seems. I mean, it’s not torture. But, there are issues when you’re dating a man who makes a lot of money and you don’t. If you’re in this situation and are facing problems you feel like can’t overcome, you’ve found yourself in the right place. After all, a good chunk of my business is setting wealthy men up with women they wouldn’t otherwise meet. And my job doesn’t stop after a good first date set-up. I often find myself being a pseudo-couple’s counselor to many of the people I set up in successful relationships. So, here are the three most common issues I see with my couples and how I tell them to deal with it.

Working all the time – Dating a millionaire

If you’re man is a self-made millionaire, he’s going to work a lot. That’s just a fact. It’s how he made is money and round-the-clock work is probably part of who he is at his core. So, you’re not going to change his work-life balance much. But, you can help him reframe some of his priorities to shift more of his time to spend with you. First, I always recommend a weekly date. That needs to be on his calendar in ink. No ifs, ands or buts about it. And I understand the sometimes the date might be a less-than-romantic lunch for two at his desk in his office. But, as long as you two get a solid chunk of uninterrupted time together, it’s a date. Second, explain to your hard-working man that a good relationship takes a lot of work, too. If you can get him to think about your relationship like he does a business venture—in the sense that it needs his time, attention, creative thinking and passion—then he’ll be more likely to meet your expectations and needs. Reframe what you’re asking of him in terms he understands. Basically, he needs to invest in your relationship if he wants any returns!

Friend meshing – Dating a millionaire

Dating a man who’s out of your financial bracket, and often out of your age bracket, can be tough when it comes to social time. You may find his friends stuffy and he may find your friends immature. My advice here is to take small steps. Don’t bring your older wealthy boyfriend out to a girls’ night of dive bar drinking. Maybe invite one or two friends over to dinner at your place instead. That way, it’s an environment both your man and your friends are familiar with. And doing a few friends at a time will be less overwhelming. When it comes to his friends, you might want to take the reigns planning there, too. Instead of a boring dinner, do an activity together, like a whiskey tasting, for example. That will give you all something to do and talk about. Plus, it will be a shared experience for you to reminisce about later. Also, understand that while both of your sets of friends should be supportive of your relationship, you guys don’t have to fall in love with each other’s friends. So, manage your expectations there, too.

Treating him is tough – Dating a millionaire

Making your man feel as valued as he makes you feel can be a challenge because he has the advantage of money. It might be hard for you to buy him a good gift or take him to do his favorite things, because those things are just out of your fiscal grasp. Here’s where you need to realize that gifts aren’t about cost, they’re about thought and effort. So, you’re going to have to get creative when it comes to gift giving. Maybe he mentioned that he really misses his grandmother’s apple pie. You might try making him an apple pie. Or, personalizing a gift can be more meaningful than getting the most expensive designer version of that gift. For example, he may be used to $3,000 cufflinks. But, if you go to Etsy and get a pair made from the menu of the place you both had your first date for a few bucks, he’ll love that pair far more than any pricey pair he has.

Know that these struggles are common and also very fixable. Focus on the love you share and creative solutions rather than dwelling on the problems and I know you two will make it through!


  • Vanessa says:

    Working past these issues is very attainable. Some of these come into play even if you aren’t dating a millionaire. Relationships require work, commitment, and sacrifice no matter the income bracket. The outcome, if in it for the right reasons, is so worth the effort.

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  • Maylene says:

    You are quite on the spot on in saying that dating someone who is really rich meant that his often too busy with his time making more money. Its quite a challenge because sometimes I feel like I am the only one who’s really eager to spend some time for us to be together. And it gets lonely too.

  • Tonia says:

    This had helped me tremendously. I am 46 he is 56 he is a self-made millionaire and I do find myself struggling when it comes to buying gifts and trying to be creative hoping that he’ll like it because it’s not something he would normally do for himself but I have found that the gifts I can afford and that I do put thought into and I customize the gift or personalized the gift he does seem to appreciate it. This article really hit home in a lot of different spots for me, now if I can just figure out how to squeeze in a weekly date it would be a remarkable because he does work a lot and so far I see him about 5 to 6 times a month. Thank you for printing this article.


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