By Baila Sebrow


I’ve been divorced for about five years, and I feel like I may be missing something when it comes to dating the second time around.

I’ve been on singles websites for a majority of this time but rarely get any suggestions. I’ve also switched matchmakers a few times. I have attended singles events where the age and type don’t match the criteria advertised, and I ended up leaving those events saddened, mostly because the crowd was much older than I was or on a different level religiously.

Then there are the dating apps. Not so great. The men I match with are either too young or do not want a serious relationship.

I have my profile circulating in the Jewish world with several shadchanim, but I rarely hear from them. I don’t get set up by friends or family. And I’ve been getting comments from friends and even my parents that maybe I should loosen up a bit, relax my standards. For example, friends have told me to dress less conservatively (a bit more revealing), or not to be so strict on my kashrut. I don’t believe in this, and I won’t feel comfortable doing this. It’s against my nature.

I recently broke up with a man I was seeing on and off since September. He was younger than I am, but mature. I love him, but it didn’t work out. My family was really against our relationship, and this put obstacles in my path and caused anxiety. He is a ger, and had finalized his process right around the time we met. He was perfect for me in so many ways but it didn’t work out, as he needed time to sort things out in his personal life. I believe if we are meant to be, Hashem will make that happen. In the meantime, I need to continue with my hishtadlut.

I frequently get comments about how great I am as a person and how I shouldn’t be single and it shouldn’t be so difficult. But it is! It makes me sad.

Am I missing something? Is there anything you can suggest, or have I “covered all bases” and the rest is up to Hashem? I may sound desperate but I truly believe that Hashem does not want me or anyone to live a life alone. It just doesn’t make sense.

I know you don’t have all the answers, but if you have any advice or words of encouragement I would really appreciate it.


Your letter articulates the unspoken words of those who are suffering silently. I will first address the issues that directly affect you. You say that you were dating a man you loved, and you continue to love him even though you broke up. You write, “He was perfect for me in so many ways.” While you do not elaborate on that, the fact that you view him in such a way is the answer to your dilemma. You may have found the man of your dreams. Hashem may have already helped you. So what is the problem? Why aren’t the two of you riding off into the sunset together to live happily ever after?

According to what you say, your family disapproved of your relationship with this man. That obstacle, and the anxiety it caused you, prompted you to break up with him. So, in essence, it was your decision to end a relationship with a man who was otherwise perfect for you. The issue may not be the websites, apps, singles events, or shadchanim who don’t have any suggestions for you. Your problem might be the choice that you have made — the choice to renounce personal joy to make your family happy.

Let’s talk about family, especially closely related members, such as parents and siblings. They love you and care about your welfare, and that’s normal and healthy. However, if they use their love to manipulate you for the sake of their honor, that is abnormal and unhealthy. And that is what I believe may have happened to you.

There are parents who are ecstatically happy when their child finds love, regardless of who the person is and where they come from. Singles who are brought up in such homes typically make wise choices when choosing their spouses, because their focus is on the chief elements that make the person who he or she is. Such people also deal with fewer obstacles when placed in the position of making the choice to marry someone or not. Conversely, those who are raised in homes where there is much rating and ranking of people, specifically about individuals who may be from diverse backgrounds, will typically find choosing a marriage partner almost impossible.

It’s hard enough to find love, something almost everyone yearns for. And having it reciprocated is nothing short of a miracle. But to also have that love blessed and celebrated by narrow-minded family members is impossible. People in situations similar to yours will either go against their family’s wishes or end the relationship. The latter is not only a guarantee for unhappiness, but is not what Torah law expects. On the contrary, one is permitted to marry the person of their choice as long as they follow halachah.

You are an intelligent adult woman. If the man you have dated was megayer by an Orthodox rabbi, then your family has zero case for preventing your relationship from running its natural course. You also mention that there are things he needs to sort out. However, if all can work out with the exception of your family’s approval, my unswerving advice is for you to follow your heart.

The other issue I want to address is the advice you’re receiving about “loosening up,” specifically as it relates to wearing revealing clothing. I promise you that in most cases, no good can possibly result from that change. Pretending to be someone you are not is not only fooling others, but yourself. For if you can’t feel true to yourself, you will lose all respect for your own identity. And bad as that is, there is even worse that can result from such radical modifications. Although kashrus is important from a halachic perspective, dressing less conservatively will convey the opposite message of who you really are, particularly to men.

There are countless women who did as you are being advised to do, and they suffered serious, non-reversible setbacks in their dating life. And here’s why. When an emotionally sound and sincere marriage-minded man is ready to get married, he is seeking a woman he can be proud to bring home to introduce to his family. A woman dressed in a manner that leaves little to the imagination is not someone a man will be proud to show off to “mama.” Moreover, the woman that a man chooses to marry is meant to be his partner in life. When one chooses a partner in any transaction, he seeks someone who is serious-minded and able to successfully carry the role. Men might date “loosened-up-looking” women and have fun with them, but they rarely marry them. Worse still is that there are men who may promise marriage to such a woman, but he will leave her when he is done. Please do not ever entertain any thought of changing who you are.

And finally, I will give you my candid response regarding the websites, singles events, apps, or any other method you have utilized where the first requirement involves a fee. You have to understand that the singles dilemma has created a major industry — the singles business. And just like any other industry, marketing strategies are employed to gain customers. Why? Because it’s about simple mathematics. Customers equal profits gained. And since this industry has strengthened due to the sheer desperation and vulnerability of clients, there is always a new entrepreneur joining the ranks.

The frum world is not that big. Therefore, competitors are competing in a small market. So what does a smart businessperson in any market typically do in the face of competition? He adjusts the prices accordingly while promising more bang for the buck by pretending that his product is better than his competitors’. And it is no different in the singles market with regard to the sites and apps. Anyone who has access to social media will see ongoing competitive wars between event promoters right before major weekends. Sadly, some of those online fights are nothing short of chillul Hashem. If you have signed up for opportunities to meet compatible singles, but the event is also someone’s business venture, then it becomes a hit-or-miss outcome for the consumer. The other issue with why you may be dissatisfied with singles events is that in the best of circumstances, where the promoter is honorable, unfortunately not all the attendees are. Sometimes singles are dishonest about their age or hashkafah just to get into a particular event.

This does not mean that singles should give up their search using all resources available, in the same way you wouldn’t give up shopping in stores for something you need. But you need to carefully research before your purchase and speak to others who have made previous purchases in the same area.

Regarding shadchanim who have not proven to demonstrate results for you, you need to bear the following in mind. If they charge money upfront, that does not guarantee they can find you a date, no matter how hard they try. It depends on what you are looking for and whether or not that type of person is looking for a woman like you (regardless of all your wonderful attributes). That creates much frustration for the single person who feels that he or she has thrown away hard-earned money. Additionally, there is no way you could know if the shadchan even made attempts on your behalf. So here, too, one must be an educated consumer and do his utmost to find out if the person he is dealing with is reputable. Or you can opt to deal with shadchanim who practice shadchanus as a chesed.

You are right that Hashem does not want you to be alone. Yet, there is no one-size-fits-all remedy for finding one’s bashert. For some it comes easily, and others endure long, painful challenges throughout their journey. However, armed with information and courage, iy’H, you will soon stand under the chuppah with your soulmate.

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


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