By Baila Sebrow



I need to know if I am doing something wrong. My parents raised me that when I take a woman out on a date, I should treat her like a princess. So I always take my dates to expensive restaurants, and I let them order whatever they want. The problem is that sometimes they take advantage of me.

For example, there are women who will order expensive wines and appetizers, even if they see that I’m not ordering the same. If I drink plain water, they will order a soft drink. Can’t they take a hint? Then, for the main dish, they order the most expensive steak on the menu. I’m not cheap, but I feel like women take advantage of me. I even had a few times where they ordered food to take out! I wouldn’t have minded if they asked me after the check. But while we are seated and eating, they order food to take out, and that makes it more expensive because the tip has to be more. I don’t want to tell them that it bothers me, but I don’t like it either. What can I do?


I do not mean to sound impolite, but where do you find such a caliber of women? For all intents and purposes, a date, especially a first date, should be considered nothing more than a glorified interview. If you were being interviewed for a job, or meeting a client for a potential deal, would you expect to be served the finest wine and most expensive steak? Even if the meeting takes place in a restaurant, can you imagine the type of impression you would make on the person you are conversing with if you indicate that you’re using the dinner invitation as an opportunity for a free meal rather than the chance to talk?

I’m going to let you in on a politically incorrect secret. There are women who go on dates just to get free meals. Yes, even among frum women. There are women who go on dates to be wined, dined, and entertained, yet they have no other interest in the man they are with. There are also women who will only marry a man who is willing to lavish outlandish amounts of money on them. The good news is that such women are in the minority. The problem is that it sounds like you are clueless in distinguishing the women who are serious-minded and well-mannered from those who are just using you as a free meal ticket.

It appears that you were raised with traditional values, and you were taught that a man must go the full nine yards in impressing his date with the best of everything. That’s nice if you are dealing with somebody who is traditional-minded, too, and not just looking for a “foodie-call.”

I want to be fair and assume that there are women who, if invited to an upscale restaurant, will think that anything on the menu is theirs for the asking. They might also believe that since they went through the time and expense on their appearance that they are worthy of being treated to something of similar or equal value. Gym memberships, flattering clothes, hairstyling, and makeup can add up to more than what a man might spend on a woman in a restaurant. Since they go through all that trouble to impress their date, they feel entitled to order the way they do. Please understand that I am not condoning their behavior, just putting this out there for you to ponder.

In addition, there are women who date extravagantly because that is what they know. They might come from affluence, and that is how dating is conducted in their social circles. For some people, it is perfectly normal when dining in an upscale restaurant to order a bottle of wine with their meal. She orders a soft drink when you drink water? Not everyone likes the taste of plain water.

Whether you are dealing with a woman who is taking advantage of you or one who innocently assumes that it is her privilege to order to her heart’s content, forgive me, but you need to accept the blame for such behavior. This clearly bothers you a lot, and so you need to be the one to take action by no longer inviting your dates to dine in pricey restaurants. I won’t even begin to comment on a woman who orders food on your bill to take out after the meal, unless you want to believe that she is either impoverished or has no time to cook another meal for a different day. But even then, it is inappropriate to do that.

I get that you want to impress your dates, and, at the same time, you are hoping that you will one day meet a woman who will have the refinement and perception to follow your lead in terms of what she orders during her meal. One might think that such traits are easy to find.

Let’s first examine the type of women you are attracted to. It sounds like you are drawn to women who have expensive taste. Such women are not necessarily taking advantage of you when they order the way they do; that’s just their way of doing things. They might also work hard for their money and they view eating out as a recreational way to relax and enjoy life. However, the red flags should start waving in your face if the woman with the expensive taste has no real job to speak of, such that she is unemployed or has a sporadic history of employment. This type of woman will not date anyone whose income does not exceed a specific number, and she makes it quite obvious in the questions she asks the man. You can easily pick up her intentions when speaking to her. Women with that nature have a sense of entitlement that is easily detected in the way they talk and carry themselves. So, if you are going to date such a woman, you need to be prepared to spend lots of money on her. Complaining will not change anything, except that she will move on to the next man willing to dote on her the way she desires.

Before you start thinking that I am advising you to date women who don’t dress well and go to healthy lengths to make themselves appealing, here is my advice on how to choose your dates. Just as there is a way to find somebody compatible in terms of attraction and like-mindedness, there is a way to filter out the subtle indicators of unsuitability, specifically where it relates to finances.

Dating is challenging for men, too. Finding the right partner with whom to share your life, who will stand by you through thick and thin and love you for who you are, is not easy. Even harder is finding someone who won’t judge you by what’s in your wallet, especially if you are attracted to women who look like they want to live a rich lifestyle. Much of the problem has to do with social media. In years past, a man might have had to worry that his significant other would want to live like “the Joneses.” But that was easily remedied by hanging out with the less-affluent Jones family. Nowadays, if you have a social media account, you will see photographs and videos of women posting about meals, gifts, and vacations showered on them. That has a direct effect on what some women feel they are entitled to, especially those who have an overinflated ego.

And it is not just the dating period. It extends into the engagement where you will be expected to buy her the ring that she has seen other women post about at the skillfully acted-out proposals. You then have the vacations in exotic locations. I’m sure you realize that is just the tip of the iceberg. There is no end to what you will be expected to provide for her. So here is the issue: Being the provider. You are the one attracted to such women, and you feed their habits — only to be resentful later.

Just as an architect designs a blueprint for the builder, you have to construct a model for what you are comfortable with. It starts with the first date. Why does it have to be dinner? Why can’t you meet for coffee or perhaps take a nice walk in a safe and scenic location? Remember, this is an interview to ascertain compatibility. If you insist on having dinner, since it might be after work and you have to eat anyway, suggest a restaurant or give her the option of a few choices where the ambience is still nice, but it’s less pricey. If she is not happy with that, or if she tells you that she only eats in such-and-such place, bid her farewell before it goes further.

If the first date progresses and it leads to a relationship, try to arrange dates that don’t always involve restaurants. For example, picnics in the park where she will offer to contribute a home-prepared dish or dessert, hiking, or other fun activities where you can spend time getting to know each other are good alternatives. I assure you that a woman who is only interested in being wined and dined for the rest of her life will never agree to such a courtship, and you will have saved yourself money and trouble in the future. Remember, money can’t buy love.

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 Questions and comments for the Dating Forum can be submitted to


Please enter your comment!
Please enter your name here