DATING FORUM

Question

I see articles about female gold diggers and everyone makes fun of women who want a man who makes a good living. But what about the male gold diggers? Is that okay? I want to bring something to your attention about what many middle-aged women are experiencing while dating. This situation happened to me and it also happened to some friends of mine.

I’m divorced, and a shadchan who deals with older singles set me up with a man who she said was wealthy and a top guy. She told me to make sure I dressed nicely for the date. I always do anyway, and people generally consider me attractive and thin. So, we went out on a date and he seemed exactly as the shadchan described him. We continued to go out and it quickly became a serious relationship. He met my whole family, etc. He spoke about marriage and he said he would buy a new house for us to live in and either sell the house he lives in or give it to his children. He told me that he even spoke to a lawyer about a prenup and things were going well.

One night at dinner, he asked me about my net worth, my annual salary, and how liquid I was. I knew what he was talking about, and I told him how much approximately. Then, in a businesslike way, he asked me, “Approximately north or south of those numbers?” I said, “Probably more south than north.” His eyes got cold, and he didn’t say much after that. He did offer me dessert, but he didn’t want any, so I sensed something was wrong right away. We still spoke by phone after that date, but he kept giving excuses about why we couldn’t get together. Then one day he called me and ended it. He gave different excuses, but I know what happened. It all had to do with money!

I was totally heartbroken. I felt used and misled by him. I told the shadchan what happened. She doesn’t care, because he writes her a big check when she sets him up on dates. I know because he told me. I have since found out that what he did to me, he’s been doing to a bunch of other women, and he only dates women who he thinks have a lot of money. By the way, this shadchan still sets him up.

This whole thing makes no sense because, why would a man who has a lot of money be a gold digger too? I’m very disheartened and I don’t think I could ever trust a man again. This happened a few years ago and I date here and there, but I can’t allow my heart to open again. After a bad marriage and this man, are there any good normal non-gold-diggers out there? My mother’s friend (who’s in her 80s) told me that back in Europe, there were men who demanded “nadan” for a shidduch, and that gold-digging men always existed. But that’s not the same thing that happened to me.

Response

Gold digging men have existed since the beginning of time utilizing different methods. For those that come from Eastern European backgrounds, there is a term “nadan,” which in Yiddish means dowry. It refers to the marriage custom where the kallah’s father pays something of value (such as a property or assets) to the chassan. In fact, this custom existed even during the Talmudic era, where it was referred to as nedunya in Aramaic. Nedunya was initially established to ensure that the daughter would receive a portion of her father’s estate, since in those times, typically, it was only the sons who inherited from the father. Nadan was so deep-rooted in the shtetel days, that a girl who was orphaned or came from a poor family, literally had little chance for marriage.

Dowry primarily carried over to present times where if a guy is considered top of the line by his community, the kallah’s father (if he could afford it) would pay all the chassan’s expenses, such as higher education, such as law school, medical school, or any other graduate program. The dowry could also include paying for the entire wedding, including all the living expenses, and sometimes includes a down-payment for a house. They also paid dowry to those men who wanted to spend their entire lives learning. And there are fathers of young ladies from well-to-do backgrounds that when they inform the shadchan that they are seeking such a shidduch for their daughter, preface that priority by stating that they will take care of all the finances, and that the young man will never lack for anything.

Though a guy entering such types of marriage agreements can be considered gold-diggers, the fact is there is nothing dishonest about it so long as all parties are upfront about their intentions. In the case that you brought to me in your letter, the man is a con artist. He presents to the shadchan as accomplished and wealthy, monetarily rewards her for shidduch suggestions, and naturally she assumes that he is a serious marriage-minded man, and any woman she matches him with is compatible with him in many aspects. If this has happened to other women too and the shadchan is aware of it, yet continues to make other women potential victims, she has become an accomplice to his game.

From the way you write, not only do you feel used and heartbroken, you also feel the system is broken. You are correct that there is a cultural bias that labels women as gold diggers when they seek stability, but when men evaluate relationships as transactions, that’s acceptable. Interestingly, not all men chase money because they need it; oftentimes, they chase it because it feeds their ego. Some people equate wealth with power. These types of men circulate freely in the dating pool. They date women whom they assume have money. When they discover that the woman does not have as much money as they believed, they drop her like a hot potato, despite the fact they were in a serious relationship and this will hurt her greatly.

These types of men are particularly dangerous to women because it makes no sense why a man who allegedly has money would target women that do too. The sickening fact is that a man can have plenty of money and still be a financial predator in relationships. Affluence can sometimes sharpen that sense of entitlement. What you encountered was not a serious suitor; he was conducting due diligence on an acquisition! Once he realized that the numbers you gave him did not align with the return he expected, his emotional investment vanished. The most painful part is not just what he did, but that he built trust first. He met your family, planned for the future, spoke about buying a house, etc. He literally did everything he could to create emotional legitimacy and trust. Your heartbreak is not just about losing him—it’s also because you realized that the version of him that you trusted never truly existed. Your relationship with him was a lie.

That kind of betrayal leaves a major scar, and it’s understandable that your instinct is to protect yourself from future scam artists of this nature. There are tragic cases, unfortunately, where men such as this marry women and then proceed to scam them out of everything to the point that the woman is left destitute. These types of men are clever enough that whatever means they use to achieve their goals, they do it legally. Yes, one can be legally scammed out of money—that’s a nightmarish fact. Please believe me when I tell you that Hashem is on your side. You cannot possibly imagine what a person like this man could have potentially done to you.

Your challenge now is not to ask whether good men exist or not; your challenge now is to spot the signs of people who confuse partnership with portfolio management. The red flags were not his questions alone; they were the speed of future promises, the grand projections, and the transactional way he viewed your finances. “We continued to go out and it quickly became a serious relationship.” Healthy people do not sell a fantasy to secure attachment. They build trust slowly and consistently.

The answer to your question is yes, there are good, emotionally-grounded, non-transactional men. But they generally do not present with fireworks, inflated promises, or polished (rehearsed) narratives. They show up with transparency and steadiness. They come across as less dazzling and not the “jet-set” type because they are offering reality, not performance (like the crook you dated).

For future dates, watch for pacing. People who create intense emotional momentum: talking about marriage, houses, legal agreements, and long-term plans, too early can create a false sense of security. Real trust is built over time, not through grand declarations. Listen to how a man talks about past relationships. Does it sound like he respects women? Con artists do not and have nothing nice to say about any woman they dated. That’s because they view women as material objects. To such men, they view a relationship that ends as a deal that fell apart. Do not allow past betrayal to make you unavailable to a future possibility. Healing means becoming wiser without becoming cynical. Your experience has given you painful but valuable data. The goal is not to close your heart, but to add appropriate filters. 

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis and shidduch consultant. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].