I am 22 years old, and a shadchan recently introduced me to a guy who is 28. At first I was not too happy about the age difference, but my parents convinced me to go out with him since he is already established. He is a professional and makes a good living. That made sense to me too, because the guys close to my age are still dependent on their parents. And my experiences with other guys and relationships have been terrible.

When I met this guy, he seemed like my prince. He is good-looking, drives a top-of-the-line car, and is chivalrous. The first two dates were amazing. He took me to fancy restaurants and wined and dined me. After that, we were just going to lounges, museums, and other places of amusement.

He is considerate of my feelings and asks me if I want to drink or eat anything. But why did he suddenly shift in the way he treats me?

We just had our tenth date, and I know that he wants this relationship to progress. My parents are worried that he might be a cheapskate. How can I be sure that even though this guy and his family are rich, he will not be cheap with me after we get married?


By Baila Sebrow

There are a variety of dating techniques that guys draw on, but rarely do styles of dating indicate future financial generosity towards a wife.

Dating is not a perfect science. There are no numerical guidelines to follow, as people have contrasting personalities and react differently to situations. Therefore, it is common to stumble into problems.

Unless a guy comes from chassidishe or heimishe circles where dating is usually conducted as “a beshow” in the home of the girl or a close family friend, his dating expenditures can run very high. Additionally, when starting out spending lots of money on dates, the guy is placed in the position of having to increase expenses, so as to impress his date even further. Some guys end up breaking up with a girl when they realize they have gone above their financial means. The guy you are dating has instead chosen to take another direction in getting to know you, and developing the relationship to a deeper level.

As a shadchan, I always recommend that guys spend as little money as possible in the early stages of dating. Doing otherwise will result in feelings of disappointment on the part of the girl, as in your case. Realistically, rarely will a guy continuously spend hundreds of dollars on ongoing dates, nor should he be expected to.

Not only are you experiencing feelings of being let down, but you appear to be demonstrating apprehension about continuing this relationship. What I find disturbing is that your parents are encouraging this mindset.

It is not wrong for parents to yearn that their daughter marry a man who will be able to financially take care of her. Oftentimes, they will recommend that she date a guy who is a few years older and more established. However, referring to him as a cheapskate because he is not wining and dining you according to their expectations is out of line.

This guy might not be taking you to fancy restaurants and running up hundreds of dollars per date. But museums and other modes of entertainment do not come for free. There is a vast difference between cheap and inexpensive.

This guy is making an effort to get to know you better. Frankly, hopping from restaurant to restaurant is hardly the ideal progression in seriously getting to know one another and determining whether it is plausible to become spouses to each other and the future parents of children. So while he may not be spending crazy amounts of money on you, he is spending something much more valuable–his time. Bear in mind that it is not just the time he is spending on the actual dates, but the research he is doing in organizing these outings to ensure that you will be enjoying yourself.

Not only that, but this guy seems genuinely interested in your feelings, as you affirm that he frequently asks you if you want anything to eat or drink. But somehow that is just not enough for you or your parents. I believe that the underlying principle might be that you were seeking your “prince.”

The problem is that your focus has been on his exterior rather than what he is like on the inside. You state that when you first met this guy, things were going great because you appreciated his good looks, top-of-the-line car, and the wining and dining. Nowhere in your letter do you comment on his intellect, personality, and overall middos as reasons for feeling that you found your prince.

This guy represented an image of affluence to you and your parents. But when that image seemed to decrease, you all suddenly began to feel cheated to the extent that you view his shift in dating patterns as a negative action.

The shidduch stage is not an easy parashah to go through. There are many trials and tribulations that guys and girls may need to overcome. That said, I usually tend to validate the feelings and experiences associated with dating. However, in your case, please forgive me, I cannot give credence to your claims against this guy.

You, along with your parents, require proper guidance to help you understand the important aspects to seek in a shidduch potential. You need direction in assessing as well as appreciating appropriate dating behavior in a guy. There are many sophisticated rabbanim and teachers who frequently offer shiurim specifically geared to these areas. I recommend that you and your parents immediately seek them out.

In the meantime, it would be sad for you as well as for the guy you are dating to miss out, on the basis of misguided notions, on the possibility of having a future together.

I urge you and your parents to communicate your feelings to the shadchan who introduced you to this guy. A shadchan’s responsibility is to be there for you from the point of introduction to the mentoring that is usually required to help smooth out any bumps or clarify miscommunication among the couple and the parents. You need to be honest about why you agreed to go out with this guy in the first place and what you expect from him and this relationship. Be mindful that he may become completely turned off once he hears of your criticisms and complaints against him.

On the other hand, it can turn out that this guy might like you so much that he may not feel offended by your grievances. And if he is financially ready, willing, and able to indulge your expensive tastes, then you might have found your match. Regardless of where this relationship goes, the lesson to be learned from all this is that dating for marriage is about getting to know one another and assessing compatibility for a future together.

Baila Sebrow is president of Neshoma Advocates, communications and recruitment liaison for Sovri-Beth Israel, executive director of Teach Our Children, and a shadchanis. She can be reached at v

Questions and comments can be submitted to

Previous articleAsk Diamond Dave
Next articleMindBiz


Please enter your comment!
Please enter your name here