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Yated Shidduch Forum 9/15/17: Redd to a Divorcee for the First Time, How to Approach?


I am a single girl and was recently redd to a divorcee. As this is something new for me, I was wondering how to approach it. What kind of questions should I ask when calling the references? What red flags should I be looking out for? If I do decide to date him, how am I supposed to react when he tells me about the divorce?

Thank you.


In recent years, quite unfortunately, rates of divorce have begun to proliferate with almost staggering frequency, and after shorter and shorter periods of marriage. Consequently, the manner by which we comprehend, process, and react to the idea of dating a divorcee has been dramatically re-conceptualized. For the most part, and perhaps this is a small silver lining to the inclining divorce rate, I believe it has led to single men and women being increasingly open to the possibility of dating and marrying a divorcee, thus opening up greater dating opportunities for all parties.

Nonetheless, it would be practically impossible to give an answer to the question of how to approach dating a divorcee, with any great degree of specificity, given only the information provided.

Are we talking about a young man of 25 who divorced after months, or only weeks of marriage, and has no children from his first marriage? Are we talking about a man in his early 30’s who has a number of years of marriage experience, and perhaps a few children, as well? Or are we discussing a man in his 40’s, or older, who was married for decades and has a sizeable family in-tow, including children he raised from infancy to chasunah? Whatever the age, if the man has children, what level of custody and involvement, if any, does he have, and how will that impact his second marriage?

Each of the above scenarios, and these are but a few of many, are vastly different from one another, and each requires its own unique approach.

As far as what questions one should be asking, in a general sense, one should start with the very same questions they would ask about a single man who was never married. The starting point, and the most important consideration, as always, is to gauge the character of the man, and whether or not the shidduch appears compatible.

In addition to the standard shidduch research questions are also those meant to learn about the previous divorce, and the obligatory vigilance needed to take note of potential red-flags. Indeed, it is these endeavors that are much more challenging and nuanced.

The overall goal is to find out as much information as is necessary about the divorce, and as accurately as possible. Meaning to say, the nitty-gritty is not really relevant, and furthermore, not the business of anyone else to know.

Succeeding at this endeavor can prove rather difficult, as the references on each side will generally advocate for the side they know. Either because that is the truth, or because it is their honest perception of the truth, albeit a conceivably misguided one. It is also possible that out of intense fealty someone may pass all the blame of the divorce onto the other side, or simply on a bad set of circumstance, even knowing that was not actually the case.

On the other hand, many of the unbiased references that are to be found, those who feel no unwavering loyalty to either side, may not have much real, concrete, or precise information to share.

What one must try and accomplish is to garner from the inquiries that are made whether or not this divorcee can be assumed to maintain a stable and healthy marriage with another person. If one feels confident that is the case, it very well may be a shidduch worth considering.

Conversely, if the information received indicates there is a reasonable expectation that this divorcee is not capable of a being in a stable marriage relationship, and another divorce is likely to ensue, it is likely not a shidduch to pursue.

In such a case, however, it is still possible that one may have some very compelling reason to believe that despite what they have learned, this time will be different. If so, the matter must be talked over with a personal Rav or mentor – methodically, extensively and exhaustively – to be sure that one is not deceiving themselves, and walking into a future disaster.

Just to be patently clear, in none of the above am I referring to the discovery of serious issues such as abuse, severe mental instability, chronic physical illness, and the like, challilah. Those are matters far beyond the scope of this forum. I am speaking only about indicators of the emotional ability to maintain a happy and healthy marriage, with the potential to endure a lifetime.

As far as how to react to the divorce on the date itself, any divorcee should expect that the person they are dating is aware of their past divorce, and should act accordingly. Therefore, being that it shouldn’t be a surprise to anyone, there is no reason not to address it head on, openly and sensitively.

It does not need to be a belabored talking point throughout the date; that is the reason for prior research. Nor do details need to be dredged up; that would be insensitive and infelicitous. But, it should politely be brought up in conversation, in order to gauge his comfort level with his reality as a divorcee; whether or not he truly seems to have moved on and is ready for remarriage; and to confirm that how he presents his perception of the past is consistent with the research one has already done.

May The Megaleh Amukos help you discern fact from fiction, and give you the acuity and intuition with which to make a wise and astute decision regarding the shidduch you have been presented with.

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