I am a 30-year-old father of a 3-year-old girl. I share custody with my ex-wife. I recently began dating a woman and we really like each other. I am attracted to her both physically and emotionally in so many ways. The level of comfort and vulnerability we share with one another is amazing and definitely the foundation for a healthy and solid relationship.

I would like to continue dating her and take things to a more serious level. She’s 36 and has three kids, two of whom are in their early teens. I know that conventional societal values in the frum and even in the non-frum world would quickly frown on such a relationship since it would seem that we are in two different life stages.

I’ve expressed to her my concern of having more children, and she said it would be something she would be open to if and when the time came. I am not intimidated that she has three kids at home, and I think I would be a great role model for them since their father is no longer frum. My friend thinks I’m crazy and thinks I am making a big mistake by dating her. To him, it’s a numbers game–an equation that must make sense. So according to him, (30 + 3) + (36 + 15, 13, 9) = Disaster. Am I missing something? Please share your thoughts and experience. Thank you.


By Baila Sebrow

Combining mathematics and interpersonal relationships will rarely formulate favorable equations. It is precisely your friend’s point of view that will likely create a disaster. He calls this a “numbers game”? My answer to him is that his calculations make no sense.

I have always maintained that people create their own personal shidduch crisis. Worse, they transmit their crisis to others. According to what you say, you and this woman have enjoyed a great relationship together in all aspects. Not only that, but you get along with her three children. That is huge. Do you know how many dating couples break up specifically because either the guy or the woman does not get along with the children of the person they are dating? Here, you appear to be looking forward to being their role model. Now along comes this friend who throws in a monkey wrench, and you begin to question the validity of a relationship so beautifully founded.

I wish I could simplify this for you by telling you to find another friend to consult with, but unfortunately that alone will not solve the crisis you have been placed in. There will always be someone in society who has an opinion that is best not shared.

In the secular world, people have no problem dating and marrying those who might appear outlandish to the rest of society. When questioned, these people feel a stronger sense of connection to the person they are dating. It is almost as though if you can shock people by your choice in a mate, you have done well for yourself. And with time, even those who voiced a negative comment will begin to speak respectfully about the person. We see this in the media quite often.

People in frum society do not share that type of thinking. Singles oftentimes choose whom to marry not so much based on compatibility, but rather how the neighbors, friends, and shul members will view the shidduch.

I have long lost count of shidduchim I suggested to singles or their parents who frivolously rejected a good idea. Now if the rejection is based on a compatibility issue or lack of attraction, I can respect that. But comments such as “this shidduch does not ‘passt’ for our family,” or “all my friends would think I am crazy for dating him/her,” is a major disappointment for any shadchan to hear. And it is my biggest pet peeve.

Let go of what your friend thinks. I say, who cares what people think? I believe if more people would adopt that attitude, especially when it comes to shidduchim, it would open up their window of opportunity. Too many people are stuck in a cookie-cutter mold of thinking, falsely believing that they need their community’s approval to attain happiness.

The problem is that their needs may not be up to par with the standards of their community. So, singles reject good potentials, in favor of those who may not be the right fit. What happens next is that they either cannot commit to a relationship that does not feel right, or they marry someone who is not on their wavelength. And we all know how some of those marriages turn out.

I do not want you to become a negative statistic because of someone else’s standards. I do not know if this woman is right for you or not, but here is what I do want you to do. Focus on this woman and the type of relationship you will potentially have with her should you both decide to get married. That is my only concern.

Now let us examine what you are dealing with here. This woman is six years older than you. On the level of maturity, do you feel that you are both on the same page? Although you get along with each other, do you share the same long-term goals? How do you both foresee the next ten years? I am not talking about situations people have no control over, such as finances and health, but the overall style of living.

Because you both had previous marriages with families, living arrangements cannot be a “let’s see what happens” approach. The neighborhood you will both settle in needs to be the right hashkafic match for your child as well as her children. Your daughter is still quite young, so we do not know where she will stand in level of frumkeit. Also, you do not indicate if your ex and this woman have similar hashkafic points of view. Since you share custody with your ex, I have to assume your daughter may take on the level of hashkafah as her mother. That might change as time goes on, and she might even become more like the woman you will marry, but it is too early to determine that now.

When blended families blend well, the upshot can be beautiful. If, chas v’shalom, it does not work out, the results can be devastating. This has nothing to do with the husband being younger than the wife. This applies also to situations where the children from both spouses are the same age.

To make a first marriage work, it is only a matter of the couple getting along with each other (OK, in-laws can sometimes pose a problem too). Any subsequent marriage, especially where there are children involved, requires that everyone be committed to making the marriage work.

In your case, you are talking about six human beings living together under one roof–while all being on the same page. That is the only issue here.

But it sounds like you are already ahead of the game. You not only appear to have established a rapport with the children of this woman, but you feel comfortable enough to step in as their role model. These kids will not only have a great stepfather, but one who sincerely cares about them. When children feel the strength of love and concern, they are eager to please.

Do you know what your real problem is? That you have waited long enough to marry this woman and set up the beautiful home you surely will.

Where this relationship is concerned, the only math you actually need to know is that two halves equal one whole. If you and this woman are meant to be together, then when your half of your neshamah will join her half, the force of that spirit will unite you as one whole.

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



Please enter your comment!
Please enter your name here