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Yated Shidduch Forum 12/2/16: Should I Try a Second Date After a Bad First Date?


My sister is currently an “older single.” She is a wonderful girl with “alle maalos” and she continues to get dates and go out. However, I find there to be an increasingly frustrating and hurtful trend of certain boys, specifically “older” ones, ending shidduchim after a first date. It is so hurtful to the girl and deeply disappointing to the people involved, who spend weeks making phone calls, researching, pushing buttons, etc.

Aside from the fact that the people who thought of and worked on the shidduch become highly discouraged, I find it terribly hurtful to the girl. All too often, my sister says, “I didn’t really see it or particularly like the boy, but I was willing to give it another shot, as I know that I am already X years old and I really want to get married.” Why don’t certain people have the same approach?

Shidduchim are not random. There are people who think good and hard before they put hours into bringing a date to fruition, thinking it was a good idea. How is it that boys, and I am sure girls as well, are not willing to give someone a second chance?


While I do strongly agree with your concern that more singles should consider going on a second date even after a first date which did not go particularly well – especially so for singles who are “older” or those who have a more difficult time getting dates – I would like to individually address the number of points you have made and review them one at a time.

Firstly, in my opinion, the most compelling reason for any single to go on a second date after an uninspiring first date, is for their own sake, not anyone else’s. There are countless stories of singles who were 100% positive that nothing about the shidduch appealed to them after the first date; no connection, no attraction, no similar interests… and yet, after reconsidering or after being cajoled by someone else, they decided to go for a second date – and then the rest is history.

How is it possible that a person who was entirely unappealing after a first date could end up being the perfect match? The answers are endless. Maybe the person had a bad day, maybe they were nervous, maybe they couldn’t get their hair to look right. Maybe the single who said no at first was having a rough day or was so stressed out that they could not see things for what they really were because they were otherwise distracted or bothered. Maybe because that’s how Hashem wants it. The why isn’t really important here. What is important is that ma’asim bchol yom, shidduchim happen in this manner.

Now, this doesn’t mean that every single time a first date goes poorly it must be followed by second one. But, if a single is being told by multiple sources that they really ought to reconsider, and perhaps they missed something the first time, it generally behooves them to try again. Or, if there is a part within the single themselves telling them inside, “Hey, maybe there is something to this idea,” it really might be worth a second look. Parenthetically, my personal belief goes a bit further, and I feel that unless the fist date was utterly intolerable or something simply unforgivable took place, it is almost always worth going on a second date before making any final decision that the shidduch should be ended.

Your sister, for example, appears to fully grasp this reality, and it is quite commendable that she is regularly willing to give a second shot to a shidduch that didn’t ring true on the first date.

Regarding your question, “Why don’t certain people have the same approach?”, I don’t know that I could possibly explain what is going on in other people’s heads, but perhaps I could offer some conjecture based on my experience.

In speaking with singles who seem to be more apt to drop a shidduch after one date, a consistency I have noticed is that these are often singles who are highly self-confident and believe strongly in their ability to assess themselves and assess others. While those are certainly fine traits to have, it can sometimes block a person from accepting that they might have misjudged a situation, because they can’t imagine they missed something. When a person is unwilling to compromise, and treats any assertion that they might be better off reconsidering a situation with asperity and contempt, that is a middah which could use some improvement.

Alternatively, other singles I have spoken with who have a tendency to go one-and-done, have expressed a concern that they don’t feel it is fair to waste their time or the time of the other single, when they are sure that there is nothing there. Again, a very reasonable, and even thoughtful, sentiment, but one that may not ultimately be beneficial to either party.

These are just two possibilities as to why others may not always see the value in a second date, and I am sure that there are many more reasons as well. Sometimes the reasons are valid, and sometimes they are misguided, and while each single has the right to pass on a second date if they feel it will not be worthwhile, I tend to agree with you that in many cases it appears to be the better decision to go for a second date and see where it leads. There is quite often nothing to lose in doing so.

There are two final points which you made that I would like to address. Namely, that singles should consider a second date because it will be otherwise hurtful to the person they are saying no to and because it is disappointing to those who spent so much time redding the shidduch and getting it off the ground.

As far as the hurt it may cause the person they are saying no to, it is of course true that before ending a shidduch one must take into account the feelings of the other single, and endeavor to end the shidduch in a way that minimizes as much as possible any hurt or pain. However, it is also each single’s prerogative to end a shidduch if they feel it is not right for them. I am not sure that is fair to say that a single must continue pursuing a shidduch that they do not feel is going anywhere because it might hurt the other person if they end it. As long as they end the shidduch in a way which is mentchlech, they have done right by the other person.

Sometimes during dating people get hurt. It is nothing we would ever wish on another, but it does happen, and it is not fair to blame that hurt on someone else who is only trying to do what is right for them as they go through shidduchim themselves. There can be hurt without blame.

Lastly, regarding disappointing those who have expended untold time and effort to get a first date to take place, that is just the way things go sometimes in shidduchim. Hakoras ha’tov is not a quid pro quo. When a single gets a date, they owe appreciation and recognition to whoever it was that set up the date – family member, friend, or shadchan. That person deserves to be thanked and acknowledged for their efforts in working on the shidduch, but they are not owed any “favors” in the form of a second date if the single feels that this shidduch is not for them.

The primary reason to go on a second date is for the sake of getting married and in appreciating and understanding that things are not always how they appear at first glance, not because one owes a second date to anyone else as recompense.

May the Chai Olamim be m’vorach your sister, and all the yechidim of Klal Yisroel, that they should be able to speedily find their zivugim without pain or hardship.

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