DATING FORUM

Question

I never thought I would have to write to an advice column, but here goes. A long time ago, I had a good marriage for a short while. Soon after we were married, my wife was diagnosed with a terrible illness and a few years later, passed away. My wife was the love of my life. She was the first real relationship I ever had. For a long time, I didn’t want to listen to any suggestions about dating. I knew I would never find someone as beautiful inside and out as she was. Then it happened years later that I met somebody and it clicked. I eventually introduced her to my family, and my sister right away told me that this lady had done work on her face and there’s no way she’s the age she claims to be. So, I did more research, and it turned out that my sister was right and she’s older.

I spoke to my rav and he said not to hold it against her and that lying about one’s age for a shidduch is not the worst thing in the world. So, I decided not to say anything to her and put her on the spot. We continued dating even though she’s older than she says. She has other wonderful qualities that I was able to look away from her age. The reason I’m writing to you is because of something else that came out.

My sister dabbles in shidduchim and she found that the lady I’m dating was posted on a shidduch chat looking for a shidduch. This time I didn’t ask anyone what to do, and I forwarded it to her and asked her why she was two-timing me and making a fool out of me. Instead of admitting the truth, she denied it and said she doesn’t know what I’m talking about and that she never asked to be posted on that chat. She also claimed that she has not spoken to a shadchan since before we met.

That was the final straw. If she had at least admitted the truth to me, I could perhaps have forgiven her if she wanted to see for one last time what’s out there. But that she lied to me…that’s not something I can live with. How can I break up with her in a nice way? Maybe I should look for a nice almanah. This one was divorced.

Response

First, I want to acknowledge your loss. A spouse who was the “love of your life,” especially when the marriage was cut short by illness and death, leaves a permanent imprint. Anyone who has not walked that road cannot fully grasp how deep that bond goes—or how heavy it feels to even consider opening your heart again. The fact that you did, years later, is not small. It speaks to courage, hope, and a desire to build again.

You also did several things right. When the issue of age came up, you sought da’as Torah. You chose generosity over suspicion. You focused on middos and character rather than externals. That is not naiveté; that is emotional maturity. But the problem you are facing now is not about age, and it’s not really about whether she was posted on a shidduch chat. It’s about truth and trust.

Let’s separate the issues clearly: Lying about age, while not ideal, is unfortunately common in the shidduch world, especially for women (and men too) who feel boxed in by numbers rather than seen for who they are. Your rav’s guidance reflected that reality, and your choice to move forward showed compassion. However, denying reality to your face, when confronted directly, is something else entirely. You were demanding an explanation that would have satisfied you fully. What you were looking for—reasonably and rightfully—was honesty. A response such as: “I was scared. I felt insecure. I wasn’t sure where this was going and panicked,” would have opened the door to conversation, repair, and possibly forgiveness. Instead, you were met with denial. And that is where trust breaks. A relationship, especially a second relationship after profound loss, cannot survive without emotional safety. If you are left questioning what is real, what is hidden, and whether you are being made a fool of, then the foundation is already cracked.

Here’s the thing. Your letter carries a lot more than a dating dilemma. It carries grief, courage, hope, and fear of being hurt again. Before addressing the practical question, this deserves to be said clearly. You loved deeply. You lost deeply. And you waited a long time before letting yourself try again. That history matters, because when trust feels threatened now, it doesn’t just sting—it shakes the ground beneath you. Let’s look at this fairly by reviewing the facts. You already demonstrated wisdom once. When you discovered that the woman you were dating was older than she said, you did not react impulsively. You consulted your rav, you took a step back and chose to focus on her qualities rather than her insecurity. That showed maturity and emotional generosity. Now that a second issue arose, this time emotions understandably took over.

Here is where context matters, particularly in today’s shidduch landscape. The reality of today’s WhatsApp shidduch groups is that they are chaotic ecosystems. Profiles are (oftentimes) forwarded from group to group without consent or copied from old chats, spreadsheets, or screenshots. Admins are focused on growing their chats to demonstrate success. Résumés sometimes get posted months—or even years—after they were originally written and shared by well-meaning third parties who assume “it can’t hurt.”

It is entirely possible, and even common, for someone to be “posted” without having the slightest awareness of it. Many people discover their own résumés circulating long after they are already engaged or married. This does not mean deception by default. It means the system is deeply flawed. So, when your sister saw the young lady’s profile and you immediately concluded that she was actively two timing you, the hurt you felt was understandable, but the conclusion may not have been airtight. The most important question is not: “Did she ask to be posted?” Rather: “Was there room for a calm, honest conversation before accusations?”

You confronted her already hurt, already angry, already feeling foolish. In that emotional space, most people go into defense mode, even honest ones. A denial does not always mean a lie; sometimes it means fear, shock, or not even recognizing the scenario you’re describing.

It’s also worth noting that you already decided once to live with imperfection when you discovered that her age is not what she initially shared with you. That decision doesn’t obligate you forever—but it does suggest that your values include compassion for human insecurity. The question now is whether you want clarity—or closure. If you want to give her the benefit of the doubt, it means slowing down enough to separate facts from assumptions.

I recommend that you arrange a date when you can speak to her uninterrupted. You could tell her that you reacted strongly when you discovered that she was posted on a chat because it brought up feelings of betrayal. Her response then, calmly without pressure, will tell you far more than a forwarded screenshot ever could.

If you still decide to end it after everything you have heard, please do so in a dignified manner. You might want to explain that this relationship is not making you feel settled and calm, and that it would not be fair to her to continue dating.

You asked if maybe you should look for a young almanah. As a shadchan I have found that a widowed person for the most part is best suited with another widowed person in terms of compatibility. There are many reasons for that, and it would take a separate article to go into those details.

You do not state your age; however, it sounds like you are not in your middle-aged years. That said, (B”H) there are fewer widows of marriageable age available to you, than divorcees. Be careful not to let the disappointment of this relationship harden into rules of widowed vs. divorced, or young vs. old. Those categories don’t protect the heart. Clarity, communication, and emotional safety do. There are widows who are guarded with the truth, and there are divorced women who are painfully honest. There are younger people who are still searching for themselves, and older ones who know exactly who they are. Do not reduce your future choices to categories out of disappointment.

Sometimes the lesson isn’t that this person was dishonest. Sometimes it’s the system that creates mistrust, and knowing what you know, you need to navigate it differently next time. Whatever you choose, choose it from a place of steadiness, not from the fear of being fooled again. You’ve already proven you are capable of love, patience, and discernment. Those qualities did not disappear. They just need room to breathe again. Your late wife’s memory does not require you to accept less than emotional safety. On the contrary, it calls you to a relationship worthy of the love you once knew. May your next chapter be built not on fear or compromise, but on clarity, trust, and genuine connection. n

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].