By Baila Sebrow

By Baila Sebrow


Unfortunately, I became single about four years ago. At first, I went out with every woman suggested to me, because I thought it would be easy enough to find a nice lady with whom to spend the rest of my life. I wined and dined them, but it never ended up working out. They were either gold-diggers or they backed out for no reason.

It’s now more than three years later, and I’ve spent thousands of dollars dating so many women. I was lied to by the people setting me up. I’m 5’7” and I weigh 150 pounds. Why would I be set up with women who weigh 300 pounds? I’m not making fun of them, but is it wrong of me to only want to date a woman who weighs my weight or less? I’ll give you one example. I was introduced to a lady, and I was told she is thin. I spoke to her on the phone, and so as not to waste my time, I asked her to tell me her weight and to see her picture. She sent me a picture of a slim, beautiful woman. As you can well imagine, I was excited for the date. In person it was clear that not only did the person who made the suggestion lie, but this woman lied, too. The woman was 300 pounds. So I made a decision that until I know that a woman is interested in a relationship and likes me for who I am, I won’t spend any money on her.

Last week, my friend introduced me to a lady who sounded lovely on the phone. I told her we should meet for a walk on the boardwalk Sunday morning and see if we are for each other. I also told her that I am serious, and that I want to see if she is in. She said that she would meet me, but then she backed out the night before, saying that it would be too cold. I heard through the grapevine that she was insulted, and the way she backed out for a raincheck was ridiculous. Did I do something wrong? I also want to mention that when I do marry, I am willing to put $2,500, or even up to $5,000, a month in the pot for expenses. I am very honest about that, and I tell that to every woman so she knows that I am generous.


The short answer is: yes, you are in the wrong. There is so much that is inappropriate with the scenario you describe, with how you now treat women, and in the way you approach dating and a future marriage. Let’s begin with the woman who dropped you before the first date. Unless you are living in a warm climate, based on when you sent your letter to me, the weather at the end of October is not ideal for a walk on the boardwalk. I’ll give you the benefit of the doubt that when you invited her for a date the weather might have been nice. But when you realized that it was going to be cold, you should have taken the initiative to change the venue for the date.

Notwithstanding, you say that you made plans to meet her and not that you were going to properly pick up the lady from her home. Why would you not offer to pick her up, like a gentleman? From the way you write your letter, you don’t sound like a youngster, so you surely know better than this.

You say that the date was scheduled for a Sunday morning. With the weather turning cold, wouldn’t it have been nice to suggest taking her out for a hot drink? It sounds like you wanted to see if she was worth the money it would cost to buy her at least a small cup of coffee or tea. Kudos to her for having enough strength of character to back out of the date, regardless of whatever method she chose for you to realize that she will never be “in it” with you! I’m sorry about your previous experiences with other women, but this woman, or any woman, is not responsible for whatever went wrong with your other dates.

I am the last person to advocate that a man should feel obligated to lavish expensive gifts and dinners on women on a first date. Not only is that inappropriate, but oftentimes it can feel creepy and even stalker-ish. However, when a man invites a woman out for a date, he should consider it no different than inviting a guest to his home. Would you not offer your guest something to drink or eat? Would you not offer a hot drink to anyone in your home on a cold day? Your behavior with regard to her feelings and needs is inexcusable.

What’s your issue with a woman’s weight? Do you assume that any woman who appears to weigh more than 150 pounds is really 300 pounds? There is nothing wrong with seeking a petite woman because that is what you find appealing. But it’s all in your attitude. Asking a woman how much she weighs before you meet her is seriously bad form and quite vulgar. Frankly, no woman should ever have the displeasure of such a conversation with a man.

I get that you have been burned, and you are probably jaded from whatever negative experiences you had in the past, but unless you do a major metamorphosis on your attitude, you’ll end up going from one date to another. Not only that, but do you realize that your closing statement comes across as repulsive? Do you actually use the words “willing to put in the pot for expenses?” regarding potential finances?

If you are serious about finding a woman with whom to share your life in a non-businesslike manner, you need to approach the possibility of a remarriage in a way that makes a woman feel comfortable, safe, and secure.

Here are some suggestions and tactics. A woman wants to be treated in a traditional role in dating. Whether or not she earns a high salary or is independent in many ways makes no difference. A woman still wants the man to take the lead and treat her with respect in addition to making her feel attractive. When you speak to a potential date for the very first time, find out what she likes to do for fun or where she usually goes on a first date. That does not mean you need to do exactly as she describes, but take a cue from the things she says. Never, ever, ever, ever ask a woman how much she weighs, nor should you ask her if she is slim or not. Try to find out that information in advance, and if it turns out that she is not as slim as you appreciate, accept the fact that slimness can be objective. What one person thinks is slim, another does not, and if a woman turns out not to be slim in your eyes, that does not necessarily mean that anyone lied to you.

I understand that you want convenience when it comes to a date, and you don’t want to do much traveling. My advice is that rather than put the woman out and make her travel, it is a better idea for you to date a woman who lives close enough to you that picking her up and bringing her back to her home should not be a major inconvenience to you. The only exception is if she insists that you meet her at a public location, or if she is the type of woman who does not mind doing the traveling for dates. That is research you will need to do well in advance of speaking with her. However, never be presumptuous either. Meaning, even if you hear that she used to travel for dates in a previous relationship, that does not mean she is willing to do that now.

When you are on the actual date, treat her as your guest. Do not make it all about yourself. Make sure she is comfortable, and don’t make it seem as though she is on a job interview. Do not shoot out random questions or demand to know personal information. Rather, view it as an opportunity to get to know each other and enjoy the time you are spending together. Tell her about yourself and give her the opportunity to speak and say whatever she is willing to share with you. Considering that it is the first time she is meeting you, avoid any serious discussions and keep it light and friendly.

If things go well on the first date, and you are both interested in continuing to date, go slow without feeling the pressure to seal the deal with a marriage proposal. In a remarriage, there are many factors to consider, and sensitivity to each other’s needs come first and foremost. Additionally, it is very important that you remain cognizant of anything that feels like a red flag to you.

If things don’t work out for whatever reason, do not treat dating as a numbers game. I hear singles of all ages complain about the number of people they have dated and that they still have not found “the one.” That is the wrong attitude. It is not about how many women you have dated or how much money you have spent in the years you’ve been dating. Nobody wants to know—not the women you talk to, and not the people introducing you to women. Having the right mindset will set the stage for your attitude and the manner in which you present to your future bashert.

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 and Israel News Talk Radio. Questions and comments for the Dating Forum can be submitted to Read more of Baila Sebrow’s articles at


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