By Baila Sebrow


Women complain about how men treat them on dates, but I want to tell you how nicely my brother treats women and how they use him for his money. He has given up on dating. The last woman he dated insisted on only expensive steakhouses and fine wines the few times they went out. My brother is not a rich man, but he is sometimes more generous than he can afford to be.

Each time he suggested a place to the last lady he dated, she said she didn’t like it, and then she would name the place she wanted to go. She told him she’s a food and restaurant snob and will only go to the finest places to eat. In the restaurant, she made sure to order up a storm: appetizers, soup, the most expensive steak, bottles of wine (she could drink a whole bottle by herself!), and, of course, dessert. Sometimes she would even ask for a selection of appetizers and desserts to be brought to the table.

On one of the dates, she gave him an item he did not want, and she told him he could sell it if he wants and that she’ll give him a cut. He is not a salesman, and he really was not interested in doing that, and he told her so. She said, “Don’t worry about it; it has no expiration date,” and she just left it in his car when he took her home.

He called me sounding very upset about how he was being treated by her and the money he was spending and that he was feeling used. On the first date she told him that she wants to see a guy investing in her!

Our whole family saw how miserable he was, and we told him to end it with her. The next day he did. Then she demanded a lot of money for what she left in his car. I don’t want to name the exact amount in case she reads your column, and I don’t want to embarrass her. My brother offered to return it to her, but she demanded the money.

My brother is new to dating and she has a big mouth, so he was afraid she would go around saying that he owes her money. He ended up borrowing money from our parents and sending it to her.

I am sure you must be thinking that there are two sides to a story and there are things I’m leaving out, but as a woman I promise you that some of my close friends admitted to me that they date only so they can be treated to fancy restaurants, shows, and vacations. It’s amazing how they manage to find men so easily who will do that for them! Now my brother does not trust women. He’s a great guy and he doesn’t deserve this. How can I help him? What can my family do?


You don’t need to convince me that there are women who use men to pay for restaurants and other expensive recreations. Such women are not looking for a relationship; they are looking for free upscale entertainment. Ironically, they manage to find that more easily than marriage-minded women looking for a healthy relationship, specifically because they don’t seek compatibility. Any man who wants to buy them steak, wine, and entertainment is good enough. In many cases, there are men who don’t want a long-term relationship, so a woman who is just looking for a few hours of fun is the one they will date.

Then there are women who are serious about finding a man to marry but they feel so insecure because of a bad previous relationship that when a new man enters their life, in their mind he needs to fix what another man did. Such women will cause the man to go the extra mile for her in various ways, one of which is demanding excessive and unreasonably expensive dates and gifts. But whether a woman is looking for free recreational fun or has emotional baggage from a previous relationship, behaving as this woman did toward your brother is simply not nice.

Being new to the dating scene, your brother did not know that this woman is a user. He should have done research on her. Most likely, this is a pattern for her. To make matters even worse, she is also a scammer, extorting money from him when the steak, wine, and other restaurant delicacies came to an end.

I am happy to hear that he has strong family support to encourage him to end it with her. I am disgusted that he was made to feel compelled to send her what sounds like an exorbitant amount of money. That is appalling and unacceptable. Women like her give a bad name to decent women.

Thank G-d, she is out of his life. Your brother now needs to learn the red flags to avoid getting involved with someone like that again.

Here is where I believe that men like your brother are wrong. Why does a man feel compelled to take a woman to dinner on a first date? A first date, for all intents and purposes, is like a job interview. Would the interviewer for a job opening feel inclined to pay for the interviewee’s dinner? Does an interviewee even expect that? A first date is the chance for both parties to be the interviewer and interviewee to discern whether there is any future potential.

Regarding refreshments, first dates need not consist of more than the man offering the woman a cup of coffee or another beverage. If he invites the woman out on a date during mealtime, or he knows that she is leaving straight from work or school to meet him for a date, then it is a considerate gesture to offer her food. But a man does not need to set up such a date. He can simply ask her when it would be convenient for them to meet for a drink. If a woman declines because the man didn’t take her out to dinner on the first date, he only stands to gain from such a rejection. First dates are not the time to wine and dine anyone. That should only come to be when it is established that there is mutual interest and compatibility.

Red flags on dates are meant to be heeded by both men and women. Since you are writing to me about your brother, I will offer advice that will hopefully be to his benefit when he feels ready to date again. It is normal to feel like giving up on dating, and it is also normal to think he could have done something differently or have been more cautious or perceptive enough to recognize any red flags.

As we all know, the past is in the past. You and your family should be validating and supporting him. Do not blame him or suggest that he was a pushover in any way that caused him to bring this on himself. Encourage him to be more vigilant in identifying what could be a toxic woman who will want to get as much as she can out of him, whether she is serious about marriage or not.

It is possible to spot problematic behavior early on. In your brother’s case, you mentioned that the woman “could drink a whole bottle by herself.” That was not just a red flag, but a red flag waving wildly in his face. He chose to ignore it. If a woman is not happy with the restaurant the man chooses, and instead suggests one that is more expensive, he should not allow her to make him feel cheap or insecure about not taking her there. Such a woman is bad news anyway, and the sooner she is out of his life, the better off he is.

Proper etiquette in a restaurant indicates that the guest being treated takes a cue from the host in terms of ordering. If the host does not offer wine or an appetizer, the guest should not ask for it. If your brother gave this woman the impression that everything on the restaurant menu is hers for the taking, then it’s on him that she took advantage of the situation. Even if that was the case, it doesn’t make her any less tacky, and he should know never to take a woman like that out on another date.

There is also the safety aspect. I am not comfortable with her imposing on your brother to take something that he did not want to take. I respect that in order to keep the entire episode anonymous you deliberately did not share what it was, but from a sensible point of view, he shouldn’t have taken it into his possession in the first place. If somebody coerces you to take something you don’t want, you throw it back at the person, if need be. By purposely leaving something in his car when he explicitly told her he is not interested in it, she clearly had some ulterior motive. Perhaps it was so she could extort money from him in the future, or maybe there was even something illegal attached to it. To give the benefit of doubt, those are also signs of a gold digger. A gold digger is interested in getting as much as she wants from her target. It is interesting to note that you indicated that your brother is not rich. To a gold digger, the target does not necessarily have to be rich. The willingness to spend money and satisfy her expensive tastes is enough to hold her interest in him.

Other red flags: women who spend the entire date discussing previous relationships, or who hijack the entire date with their narrative about whatever subject they are talking about. The people a woman keeps company with or is drawn to in relationships tells a lot about her too. As the saying goes, “Show me your friends, and I’ll show you who you are.” If the woman expresses jealousy of those who have more in any area of life, whether it is money, status, possessions, etc., that is not a healthy attitude. If anything bothers someone while they are in any sort of relationship, it is best to bring a discussion about it to the table. There are times that what seems to be a red flag is just miscommunication. Regardless of who is feeling ambivalence in the relationship, it is of utmost importance to get answers to questions that feel disturbing.

In the future, iy’H, when your brother dates a normal, healthy woman who wants him for who he is, she will be happy with whatever thoughtful gesture he demonstrates, even if it has little to no monetary value. Anyone who spots red flags in a dating relationship must trust their instincts. If it doesn’t feel right, it isn’t.


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. She can be reached at Baila also hosts The Definitive Rap podcast for, Israel News Talk Radio, WVIP 93.5 FM HD2, and Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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