Oy! What Should My Son Do?

Oy! What Should My Son Do?

By Goldy Krantz

I received a letter very recently from the mother of a man looking for advice. I’ll let you read what his dilemma is, but I first want to preface that I encourage all to use their seichel in these types of situations. When I answer emails (whether I publish them or not), I always try to put myself in the position of the email writer and think, “What would I do?” or “What if I was on the receiving end of what I’m advising someone to do? How would I feel?” There is no “right answer” to many of the issues people write about. There are just answers of what makes sense to do. I have never touted myself as a Dear Abby or a know-it-all. My advice is what you may receive from a level-headed friend who has seen it all and experienced most of what the shidduch world has to offer.


Dear Goldy:

I’m writing to you for my son, David [not his real name]. He refuses to write to you, but told me that if I wrote to you, he would read your answer and consider taking your advice, “depending on what she says.” I don’t know how often you read your mail, but this is an urgent matter, so I hope you read (and answer) this soon.

David is 40 years old. He has lived on his own for a while and I have been out of his dating life from even before that. He always spoke with shadchanim or friends and arranged things on his own. He would tell me when he was going out with someone only when he was in the mood. I’m sure there are several women that I am unaware of, whom my son has dated. But I do know of some. About three years ago, David had told me and my husband that he was dating a particular young lady for “a while” at that point. He said that she was just about everything that he was looking for: She was very pretty, had an adventurous side to her, was an accountant, they shared many interests, and their hashkafos were just about the same. My husband and I ended up meeting her by happenchance. We went out to dinner with friends, and as we were leaving the restaurant we bumped into David and this young woman walking into the same restaurant. It was not planned at all! She seemed sweet and had an air of sophistication in the way she carried herself and spoke. My husband and I were impressed with her. A couple of months passed and, as far as I was concerned, David was still dating this woman. But then I found out that they broke up. I don’t know what the reasons were, but I know that it wasn’t my son’s decision. David took a few days off from work following the break-up and went to visit some friends in Florida. I know that David was disappointed about what had happened. It was evident by his behavior and the way that he spoke in weeks that followed.

Since the call, my son said that his brain has been stuck in overdrive. He said he keeps thinking of “what if” with the girl from three years ago

Fast-forward three years and why I am writing you. My son started dating someone new about a month (or a little over a month) ago. I don’t know many details, but David seems happy. Last night David came over to speak with my husband and me. In a nutshell he said that a mutual friend of his and of the one he went out with a few years ago contacted him and told him that the woman wants to go out with him again, if he was interested. David said that he really liked her, but was devastated when she broke up with him. He said it took him weeks to recover. Added to that, he started dating someone else whom he says he likes. He said that his feelings for the new woman are different because she is her own person, but he still has feelings for the first girl.

He doesn’t know what to do. He’s torn. I asked him how he truly felt about the new girl that he’s dating. He said that he would be very happy dating her had the friend not contacted him. Since the call, my son said that his brain has been stuck in overdrive. He said he keeps thinking of “what if” with the girl from three years ago.

David is a good man. He doesn’t want to lead on one girl while dating another. He doesn’t play the field. We don’t know the future. We can’t know what will happen if he continues with the new girl or starts again with the other one. There are no guarantees. David said that he told his friend that he would call him back with an answer in a couple of days, once he has had a chance to think things through.

Goldy, do you have any advice for David?

A Concerned Ima

Thank you for writing. Wow. I’m sorry that David [not his real name] is going through this. Dating is hard enough, and just when he thinks he has things figured out, he gets a curveball thrown at him.

Again, this is an issue where there is no right answer. David has to decide what to do and what feels right. You hit the nail on the head when you wrote, “We don’t know the future. We can’t know what will happen if he continues with the new girl or starts again with the other one. There are no guarantees.” If David continues with the current woman, would they be seeing each other under the chupah in the future? Would he see the one who broke up with him three years ago, if they started dating again? Would he see either of them? David could marry the mystery woman behind door #3. We don’t know.

You didn’t include it in your email, but I’m sure that you, your husband, and David discussed why the relationship didn’t work three years ago. The reason should play a big part in his decision. Maybe he can speak with the woman from three years ago and discuss the reason why she broke it off with him and ask if that reason is still prevalent, or what has changed in her life to make her realize that she would like to try dating David again. That may help David in making a decision.

I love that you wrote, “David is a good man. He doesn’t want to lead on one girl while dating another. He doesn’t play the field.” All too often I have heard of men dating two or three girls at a time. Yes, I know that I wrote of doing that myself. In my defense, I will add that I agreed to go out with all three before I even had a first date with any of them. I had been having a dry spell (a drought really) and hadn’t gone out in about six months when three phone calls came in during a 48-hour period. I jumped at the chance of maybe finding my husband in one of the three. I also knew that I wouldn’t be breaking any hearts by triple dating and that I would probably not date at least one of the fellows more than once (knowing my track record). So I felt safe in what I did. David has been dating the new woman for a month. It is too far into the relationship to start double dating, especially with someone he has a history with.

My advice: David should speak with his friend and tell him about the reservations he has about dating the woman who broke his heart, so the friend can speak with the woman. Maybe he should even call the woman herself to discuss it, but some would feel very awkward having that discussion. Anyway, David has a right to know all the answers to his questions before he makes a decision. This way he can make an informed choice. The friend can act as a middleman or can relay the message to the woman and ask if they can have a frank discussion. Remember what you wrote: We don’t know the future, but we do know that we are dealing with two women here and both have feelings and we also know that David is kind and doesn’t want to hurt either woman or himself.


Goldy Krantz  is an LMSW and a lifelong Queens resident, guest lecturer, and author of the shidduch dating book, The Best of My Worst and children’s book Where Has Zaidy Gone? She can be contacted at bestofmyworst@hotmail.com.


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