DATING FORUM

Question

I’m 40-years-old and have never been married. I dated a lot but never met the right guy. It was either that or they didn’t want to go out with me again. I recently met a wonderful guy at a singles event. He’s funny, sensitive, and has all the qualities I’ve been searching for in a husband all these years. The problem is that he’s divorced with kids and from what I hear, it was a very messy divorce. My parents, friends, and even my rav are trying to talk me out of seeing him.

I really want to pursue this relationship and get to know him better. Should the fact that he made one mistake in his life be held against him, even if the divorce was his fault? Isn’t it possible that he can turn his life around and be an amazing husband? My family says I should wait to meet someone else who’s in his 40s and doesn’t have children and a complicated history.

I’m worried that I may never be able to have children because I didn’t freeze my eggs and women in my family have a history of early menopause. The guy doesn’t care because he already has kids.

What’s your advice?

Response

Your letter comes across as honest, vulnerable, and very frank. I’m going to answer you with the seriousness it deserves, not with clichés, not with fear, and not with fantasy. You are forty. You’ve dated and it sounds like you patiently waited. You have not lost hope. You have walked away when it wasn’t right. That’s not failure—that is discernment and survival in today’s dating world.

Now, for the first time, you have met someone who feels different. He’s funny, sensitive, and surely emotionally present. He has the qualities you prayed for. That’s not something to dismiss lightly. Nor is that so easily found. But now comes the complication: he’s divorced with children. And if that wasn’t an obstacle enough, the divorce was messy and possibly even his fault. You are fine with all that, accepting him as he is, yet everyone around you—parents, friends, even your rav—is sounding the alarm.

Let’s unpack this carefully. Is divorce automatically a red flag for someone who has never been married? From a rational perspective, no. But it is always information. A divorced man is not “damaged goods.” He is a man with a history. At 40-plus, almost everyone has history, whether it’s divorce, broken engagements, long relationships, trauma, financial mistakes, or emotional baggage.

The question is not “Did he make a mistake?” The questions are: Has he taken responsibility for it? Has he grown from it? Does he speak about his ex-wife with accountability or with blame? And the most vital question of all: Is he emotionally stable today?

There’s a massive difference between a man who says, “My ex was crazy, everything was her fault,” and a man who says, “I failed in areas, but I went to therapy. I learned, and I’ve done the work.” If he owns his part, even if it was ugly and messy, that’s maturity. If he minimizes or rewrites history, that’s a dangerous red flag.

Let’s discuss what a “messy divorce” can actually mean. Messy can mean many things. It can be a long legal battle, custody conflicts, financial disputes, emotional volatility, or none of that, but just community drama where everyone talks about the divorce, yet there is very little truth to the rumors. The bottom line is that “messy” doesn’t automatically equal “bad husband material.”

Realistically speaking, divorce is almost always messy when children are involved. There is tremendous pain all around when a family is fractured, but that doesn’t and shouldn’t define who they become afterward.

You need to clarify and find out if the conflict is still ongoing or if there is peace now. If the ex-spouses are still at war, then marrying him will drag you into the middle of it. That is certainly not how you would want to spend your shanah rishonah. You must also find out how he relates to his children, and if he co-parents respectfully. If the chaos is still alive, you’re not just marrying him—you’re marrying pandemonium. If it is resolved and he has stabilized, that’s a different story.

Your parents are also telling you to marry someone who doesn’t have children. The children factor is not small. Marrying a man with children means you are usually not first in his life because his time, finances, and emotional energy are divided. Moreover, whether this is something he can admit to you or himself, his ex-wife will always be in the picture in some form. That does not necessarily make him a bad candidate, but it makes the structure of your future look very different.

There are many successful marriages where one spouse has never been married and the other is divorced with children. For such a marriage to work, you must ask yourself honestly if you can handle sharing him prioritizing his kids over you on occasion and the inherent stepmother dynamics. What about discipline? What is his approach to discipline and will there be a conflict there? The other issue, and I’m sorry to bring it up, but what if his ex-wife ends up being the only woman who bears his children? How do you foresee handling that? Some women thrive in all those situations, while others slowly grow resentful. You will need to do some serious soul-searching to ascertain how you would handle it.

I would like to further elaborate on your fertility fear, because that part is emotional and real. You are aware that biologically, time is limited. You also have a family history of early menopause. That adds pressure. Are you drawn to him partly because he removes the pressure of “I must have children”? You say that he doesn’t need more kids. Does that make you feel safer? Please ask yourself: If you met an equally wonderful man who had never been married and deeply wanted children, would you still choose the man you’re dating instead? If your answer is no, it’s possible that fear is influencing your decision. If the answer is yes, and this man genuinely feels right, that’s different. Never choose a husband because he lowers your anxiety. Choose him because he raises your peace.

If it was just your parents that are opposed to this shidduch, that would not be unusual. Sometimes parents (and friends) operate from fear because they see patterns. The thing is you’re saying that your rav is against this shidduch too. That’s an important aspect, not to be overlooked. Sometimes rabbanim are cautious about messy divorces because they’ve seen the damage firsthand. So, instead of dismissing your parents, friends, and rav, ask them directly what their concerns are. Is it about his character, divorce details, financial or emotional instability, community reputation, or is it about his children’s mother? Their objections cannot be vague if they want to be taken seriously. They must be specific. Meaning, if they say something like, “It doesn’t look good for the family,” that’s not strong enough.

What you should focus on is that it’s possible for a man who failed once at marriage to become an amazing husband. But there are caveats. It depends entirely on whether the failure humbled him or hardened him. Meaning, there are men who become deeply self-aware; they value marriage more, they appreciate partnerships, and have grown emotionally. Those are all good signs. If after their divorce they get defensive, blame women, and carry resentment, you can expect repeated patterns from such a man in a new marriage. Watch how he handles disagreements with you, whether he apologizes, takes feedback, and is consistent. Early charm means nothing. Character shows through tension.

Here are some brutally honest questions you must ask yourself: If he had never been married and had no children, would I hesitate at all? If I were 28 instead of 40, would I choose him? Am I ignoring red flags because I’m tired of dating? Do I feel calm around him, or just excited? When I picture the next 20 years, do I feel stable or anxious?

My advice to you is to continue dating him slowly. Ask hard questions. Observe how he co-parents with his ex-wife, but meet the children only if things become serious. Get clarity on finances and custody. And in these types of relationships, I strongly advise premarital counseling.

My final thoughts are that being divorced is not the issue. Children are not the issue. Your age is not the issue. Unresolved character flaws are an issue, as is unmanaged chaos. I will leave you with this: Desperation whispers, “This is my last chance.” Wisdom says, “If he is right, he will still be right after careful evaluation.” Date him with your eyes wide open and choose from strength, not scarcity. 

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. Baila also produces and hosts The Definitive Rap podcast for 5townscentral.com, vinnews.com, Israel News Talk Radio, and WNEW FM 102.7 FM HD3, listenline & talklinenetwork.com. She can be reached at [email protected].