Dating Someone with Money

It sounds great on paper – dating someone with money – but there are special considerations to take if you decide to pursue or date someone who has a lot more money than you. Yes, dating someone with money has a lot of advantages in that he or she offers the prospect of having a nice home in a good area, fancy vacations, and the chance to engage in activities and outings that many others can’t afford. But everything has a cost, and you should be aware of all the issues that can come with dating someone with money when you have a lot less money yourself.

Wealthy men and women often fear that people want them for their money.

The biggest challenge you’ll face in dating someone with a lot of money is the fear he or she has that you will like him or her because of the money and that you’re looking for a free ride. Sometimes men and women write in their dating profiles that they are looking for someone who is financially successful, but I highly advise against this practice. This, in fact, is the type of behavior that makes wealthy singles feel insecure and worried. If you date someone with money, make an extra effort to suggest date activities that involve middle-of-the-road costs. If you’re suggesting a restaurant, suggest a common one rather than a five-star restaurant with velvet ropes out front; if you’re suggesting a weekend away, suggest an average hotel instead of one known for top-of-the-line amenities and services. By doing this, you are sending a clear message that you are interested in getting to know that new person better, not trying to milk him or her for their money.

Watch out for the tendency to idealize the wealthy.

Dating someone with a lot more money than you sets you up for something that is extremely tempting: idealizing him or her because they have money. If you get picked up in a fancy car and whisked away to a fancy restaurant, you’re probably going to enjoy that. If you end up liking your date’s personality, it’s even more tempting to tell yourself that this person Has It All and that you would be perfectly happy with this partner. Remember that money is all about the surface, and it’s only after months of getting to know a person that you see their true personality and character. The truth is that wealthy men and women have just as many hang-ups and emotional issues as their less well-off counterparts, so catch yourself if you start idealizing him or her.

Don’t give in to your own insecurities about how little money you make or have in comparison.

Listen: money shouldn’t mean that much. Looking for someone with money is bad; looking for someone who is established – you know, has a job, health insurance, and enough money to take the occasional vacation – is good. The bottom line is that there is no fairness in the way people get paid. Some professions are paid extremely well while other worthy and important professions – teachers, childcare workers, and others – are paid minimally. You should feel good about what you do or you need to create a plan to change jobs or fields if you don’t feel good about what you do. Moreover, you should accept that some professions simply aren’t valued. In other words, a preschool teacher should feel just as proud of his job as the executive banker who makes five times the teacher’s salary. Show your wealthy date that you value your profession and that you understand that your low pay is no reflection on your overall merit or worth as an individual. (Never forget that confidence is the world’s greatest turn-on.)

Questions to ask yourself with someone rich, poor, or somewhere in between…

Does he treat me well? Do we have similar interests? How much do we have to talk about? Does she get my sense of humor? Does she have friends with whom she has good, close relationships? Is he affectionate and does he pay me enough attention? Is she already professionally established or does she have a plan about what she wants to do professionally? Is he someone who would make a caring, attentive dad? Is she sensitive to my feelings and the feelings of others? These are the questions that matter, not the question about whether he or she has money. Yes, you can find someone who has money and who has the personality traits you value, but it will only last with that person if you don’t value their money too much.