Dating Someone You’ve Already Dated

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    There are a lot of posters in the CR who have lots of experience in shidduchim, I have a question I could use some help with.

    Hypothetically speaking, of course ;-), if a boy and girl go out for a while, let’s say more than 4 dates. They seem to be compatible hashkafah wise and they get along well. Something happens (maybe one date didn’t go well) the boy agrees to another date but the girl decides she doesn’t want to go out anymore. Boy decides he has to move on and go out with other girls. Some time goes by he’s gone out with other girls and his experiences with the other girls make him think that what he had with the first girl was more “real” and is worth pursuing. Is it OK for him to ask the first girl out again or is she the one that would have to change her mind first? If it is ok for him to ask her, is there a certain amount of time that should go by first or an amount of girls he should go out with before asking her?

    Thanks in advance for your answers


    Have it re-redt and go out. It will go much faster either way a second time around. Good luck!


    Go for it. Worst thing that will happen is she will say no. Why wait if you think she could be the one?

    Just don’t make it seem pushy.


    IMHO if you really think that 1st girl is for you, find out if she’s still interested. and if so ask her out. Take a chance. I did and it worked out for me. You’ll never know until you try, and if you don’t try you’ll always wonder.

    NY Mom

    I often hear stories of people who go out again and end up getting engaged the second time around. My advice is to approach the shadchan and ask if he/she could contact the girl and see if she would agree to go out again. I don’t think there is a certain amount of time you need to wait, just have the shadchan feel it out rather than you calling her directly yourself. It is better that way because if the girl is busy or really would not consider it again, it is less awkward.

    Hope that helps and hatzlochoh!



    Add one more voice to the chorus of yeses.

    I know of at least two cases where a “no” ended up with a B”H happily married couple.

    Since the girl was the one who said no, I strongly agree with “NY Mom” who said a third-party shadchan should be used – it could be very uncomfortable and even seem stalker-ish to call a girl directly after she said “no”.

    Hatzlocha raba.


    Thanks for all the answers, I’ll probably think about it for a while longer but assuming I decide to try it again, I have a small point I’m not sure about.

    I know there’s a thin line between going with your gut and being a creep, so I figure I should not contact her directly. On the other hand I feel like if I just had a shaddchan ask her if she wants to go out again without being able to explain my reasoning there’s no reason to think that she would say yes. If there’s one thing I learned from this it’s that the more people involved in a shidduch the more confused everyone gets. Would it make sense to ask the shaddchan to see if it would be ok to send her a message via email or something like that?



    E-mail is a creepy and gutless form of communication.

    The only thing worse than that is to ask her out on a blog comment!!

    NY Mom

    IMO, just let the shadchan do the explaining. You can even write it out for the shadchan, so that what you are trying to say is crystal clear , but I’d stick with the shadchan as the go-between. Or when the shadchan calls her to ask her if she would be willing to try again, you can have the shadchan say that you would be willing to go into more detail in an email and see if she would be open to that.


    artchill, Of course I would prefer to say what I want in person or over the phone but wouldn’t that be harder for her? So what would you say to do, tell the shaddchan what I think and trust them to tell it to her properly?


    I’d have it re-redt, but with a new shadchan, as its doubtful the original one will be as motivated the 2nd time.

    If it works, the $ can be split between the 2 (and of course, be sure to level with shadchan # 2, so there are no surprises)



    How about a family member of hers. It he/she says: “I saw itsallyourfault and he wishes he could get a second chance” or similar, that would be more informal but still allow her not to say no to your face.


    NY MOM, you give good advice, Thank You.

    BP Totty, that would be difficult b/c the shadchan was a family member, but you actually gave me a good idea that I probably shouldn’t post here, thank you.

    NY Mom

    BP Totty and gavra_at_work: I disagree with this. He should first check with the original shadchan to see if he would be willing to contact her, before going to look for a 2nd shadchan.

    itsallyourfault: I am speaking from personal experience here. When I was dating, I was once approached by a shadchan (the original shadchan who knew e/t about the shidduch) to “try it again” one year later since both of us were still single. I thought about it, but said “no”. It would have been so uncomfortable had he just called me out of the blue and I had to say “no” to him directly.


    Whoopee! Does that mean I also get a cut?

    NY Mom

    itsallyourfault: You’re welcome 🙂

    I really wish you hatzlochoh and you should find your zivug hagun b’karov!


    “Whoopee! Does that mean I also get a cut?”

    Getting a little ahead of yourself there aren’t you?



    It is normal, and happens many times the second time around.

    I know a guy that the third time around, both him and the same girl decided

    to go for it. I even know of a case where ther girl said no, the guy was still

    interested, asked the shadchan 8 girls later and turns out, after 5 boys later,

    the girl realized she made a mistake but was embarrassed to ask the S to retry, till S called girl. They’re happily married now.

    Do not e-mail, creepy and to forward. Don’t worry if yu get turned down,

    at least you tried and she know where you stand.

    (perhaps she has to go out with some more schlemiels, till she gets some sense.)


    NY Mom: I know it sounds horrid, but I meant doing so without the shadchan (but giving the shadchanis if it works).

    If they have gone out on “more than four dates”, they can restart without a shadchan if needed.

    Anonymous Person


    Most certainly go for it.

    As a girl shidduch dating for many years I have learned a lot. I have definitely made mistakes and maybe the one you are thinking of has too. As hard as it is for you to put yourself out there she may find it way to difficult to even broach the subject with anyone to even do something about it. Reach out to her; you may be pleasantly surprised.

    I have had individuals, through a 3rd party and directly, ask again with various outcomes. I know of 2 people personally who are now happily married and sometimes it was becouse of a miscommunication on her, yours or a shadchan’s part, but not to a/o’s fault.

    Good Luck.


    “I strongly agree with “NY Mom” who said a third-party shadchan should be used -“

    I do, too, buit only because it is a good way to save face, not put preswure on either party, and if it’s yes, great, if no, then nothing ventured, nothing gained. I would go for it, definitely. She can only say no, and if it otherwise was going well to that point when they agreed to stop going out, it might go again.


    I agree w/ oomis1105’s reasoning. Go for it.


    I know someone that this happened to and they got married!!

    but before you dump the first shaddchan remember they would have to get paid either way if it works out.


    date the girl again,i know lots of ppl who dated again..and got married!!


    Again, I appreciate all the advice, I’m going to wait a little longer before doing anything, I’m just not quite ready yet. It definitely helps to know that I have the option when I’m ready, sometimes the dating “rules” can be very confusing.


    First of all, if I were itsallyourfault I would change my username before getting into a marriage situation.

    Also, when you say “They seem to be compatible hashkafah wise and they get along well” are you sure that it is not just that “they get along well” and that is why they “SEEM to be compatible hashkafah wise”?

    Having been in a similar experience, I realized that the girl is never going to say “you’re not frum enough for me.” Instead, she will make up some silly excuse so you can never figure out why she is really not interested. Reading between the lines, I would say you should try to figure out if you really ARE compatible before getting into an uncomfortable situation.

    Best of luck!


    “First of all, if I were itsallyourfault I would change my username before getting into a marriage situation.”

    I could always change it to “itsallmyfault” but honestly the username is not reflective of my attitude, it’s kind of a joke.

    “Also, when you say “They seem to be compatible hashkafah wise and they get along well” are you sure that it is not just that “they get along well” and that is why they “SEEM to be compatible hashkafah wise”?”

    The reason I used the word “seem” is that there is no way to know for sure if the other person is being honest or just agreeable. That said, I don’t think that’s the case here b/c there are some details that I left out of the story for privacy reasons that make it “seem” like something else was bothering her which could be a reason not to go out again but also could be just a misunderstanding. Anyway, there is no way to know for sure without asking.


    Come to think of it, I’ve dated someone I’ve already dated and it worked out just fine. In fact, I’ve probaby gone out with her close to 800 times, and so far so good! (If you have’nt already guessed, I’m talking about my wife)


    Well obviously without knowing the details, it is hard to judge (not that we want to judge you, chas veshalom!)

    But I still maintain that you should have a valid reason to think she may change her mind before putting her (and you) through the pain of considering it again, since obviously there is a reason she said no the first time around.

    I don’t mean to sound harsh, I’ve just been there, and I know what it feels like.

    Hashem should give you siyata dishmaya to find your zivug hagun bekarov, and easily.


    Sometimes the first time around, one of the two is really not ready to be dating, or really does not know what he or she wants. I have seen people who broke it off after a few dates, then ended up reconnecting two or three years later, when they were both more ready, and got married.


    “But I still maintain that you should have a valid reason to think she may change her mind before putting her (and you) through the pain of considering it again, since obviously there is a reason she said no the first time around.”

    That’s the hard part, thanks for the advice.


    oomis, that is true. But it is also possible that at the beginning one of the two does not know what he or she wants, but then breaks off the relationship when they do realize what they want. Which may or may not be the case here.


    I know a number of people who stopped dating someone for any number of reasons and some time later (in one case, almost 2 years later) the shidduch was brought up again and the parties agreed to date again. I personally know of 5 such instances that resulted in a marriage, while some of the other couples stopped it again after several dates. People grow wiser and learn new things about the world and about themselves as they grow older and the person who dated 6 months ago, may be a different person now.


    That is very true. I wouldn’t want to be responsible for preventing a shidduch from coming about. Maybe the best idea is to speak to a mentor you trust, to whom you can tell all the details, so they can get a clear picture of the situation and help figure out what’s best.


    I recently attended a chassunah where after 4 rounds of dating (not a typo!) they finally got married.

    Please no comments of “they don’t know what they’re looking for ” etc. We can’t judge & don’t know the details.

    I’m sharing this only as a small piece of chizuk for those that are willing to give it another go. That’s all Hashem wants from us, is to try.

    Hatzlocha rabba!


    I have not read the comments on this post (kind of busy at work).

    I have actual experience in this topic. I dated a girl for a few weeks and then we decided to end it for whatever reasons we had. About two months later, after talking it over with mutual friends and my mentor, we decided to get back together. It still did not work out, but we are friends now and there is no animosity.

    (Some of) The advice that I was given when I decided to date this girl again was that I can’t just date her for one or two dates. We had to go out for a couple of weeks, to really make sure that we are for each other or not (even if we had new issues with each other we should discuss them with each other and work them out if possible, not to keep them “bottled up”). This would then preclude us from having to go through the whole scenario again. Also, it was advised to us that whatever problems we had with each other the first time around we had better make sure that it was resolved or else it will be fruitless to go out again.

    I would pass this advice onto whoever decides to go out with a girl/boy they have already dated.

    Personally, if both the girl and boy want to go out with each other again after they broke it off once, they should. But make sure that whatever issues were on the table the first time around are resolved, or else you will just be going through the motions again.


    “That is very true. I wouldn’t want to be responsible for preventing a shidduch from coming about. Maybe the best idea is to speak to a mentor you trust, to whom you can tell all the details, so they can get a clear picture of the situation and help figure out what’s best.”

    Don’t worry about it, I’m not going to base my decisions entirely on advice of anonymous posters, I would definitely discuss with someone I trust.


    Firstly I want to tell you that I certainly understand that the shidduch parsha is quite a difficult one and a serious one. It is not as fun as kids think it is going to be. If you are lucky to hit it on the first shot, meaning if Hashem truly blessed you and sent both of you your basherts right out of the gate, you truly would have been the luckiest people, because it would save you from the heartache of dating.

    I know people laugh and make fun saying “don’t marry the first girl, or the first boy, you wont have anyone to compare them to. The thing is why do you need to compare? You have to judge each shidduch on its own merits and not be looking over your shoulder or around the corner for what else is out there. Comparing is a waste of time because it never stops. You just have to work with what Hashem sends you and see if this shidduch will be a good companion for you, a good parent to your children, a good spouse, a good partner, a good role model. Is there a physical attraction? Is there an intellectual connection? That will lead and build to an emotional connection.

    Having said that the question I would ask you is this, what could you have done differently at that time to bring about a different outcome? Did you show the real you? Did you act appropriately? Did you do anything you shouldn’t have? If there is something you could have or should have done differently that would have kept the process going, then having realized that it would be worth pursuing. Humbling yourself by contacting the shadchan recognizing that you made a mistake and you might have given her a wrong impression of you, or you might have unintentionally offended her or turned her off, and that you would be honored if she gave you a second chance, might portray you in a new light as far as she is concerned.

    However, if there is nothing you would have or could have done differently back then, and there is nothing about you that you know for fact that was in your control that caused the break up then you have to consider the fact that maybe it just wasn’t bashert. Understand that you can’t change other people and you shouldn’t change yourself to please other people because you will never be happy and it won’t work out in the end. Many people in such a situation think “I can change to please her, I can be who she wants me to be” and that doesn’t work. So I am hoping that is not the case with you. If she is looking for something that is not in your make-up or not in your skill level, or not in your personality then let it go.

    However, as I said, if there is something worth pursuing because you think it was a misunderstanding and you can actually easily be on the same page go back to the same shadchan and be honest and straight-forward; brace yourself for rejection because it could happen but its worth it if on the other hand you succeed.

    It is absolutely true what people have said about the second time around and how happy they are, but it is also true that the divorce rate has risen tremendously among young couples. The commitment to hang in there and keep making it work is just not there. Young adults going into marriage for the wrong reasons, choosing their spouses on the wrong criteria, thinking that they can change each other to bend to their own requirements is just leading to heartbreak, dysfunctional and broken families and children who are lost and in tremendous pain. So I say this with the utmost and sincerest blessing for your success and happiness.

    If you have the confidence that there is something worth pursuing by all means go for it!


    Aries, I don’t think it is a matter of comparisons to date more than one person. I think that some people so romanticize the notion of shidduch dating as an end in itself rather than as a means to an end, that they could actually convince themselves that the first one is THE one.


    aries2756: I don’t think I did anything particularly wrong when I was going out with her, there are some things I would have done differently but nothing major. I understand what you are saying about not trying to force things, I’m not looking at it as if I have to go out with her again and then everything is going to be perfect and we’ll get married, although that would be nice. I am thinking that it is possible that the problem is just a misunderstanding or possibly that she just wasn’t ready (there is a good reason for me to think both of these) and that if I go about it properly it can only be a good thing. If she says no at least I did my part and she would know how I feel and that alone would make me feel better. I know that if it’s meant to be it will be and if not not, as long as I do my part.

    As far as changing to please someone, I’m very honest about who I am and I’m not going to change but I think (hope) it’s possible that marrying someone “better” than me would make me better in some ways. Does that not happen?

    Thanks for the advice


    When you say there are some things you would have done differently, it’s possible that those are the things that bothered her. To you they may have seemed to be nothing major, but maybe to her they were. Maybe aries’ suggestion of humbling yourself, in recognizing what you may have done “wrong” (in her mind) might work. If she sees that you recognize what made her uncomfortable, maybe she will respect you for that recognition.


    I find it very acceptable and normal to go out with someone you’ve previously dated, even though at that time it didn’t particularly work out.

    Everything happens for a reason. Maybe they weren’t “meant” to be wed just yet. Or perhaps some time has passed, and one or both parties matured since then. There are several explanations for situations such as this.

    I have seen this happen many times in the shidduch/dating realm.


    It is quite common for couples that have already dated to date again. Sometimes, one thinks – there must be someone better, smarter, prettier, more charming etc out there. When they date more guys or girls they see that there is not. The sorry story is when you want to see an old date again and the guy or girl is already engaged or married. This I find to be even more common.


    Phyllis, I wonder if u know how true what u r writing is.



    i had a similar situation happen about a month ago. There was a girl i dated a few years ago and without my asking a different shadchan re-redt her to me again. I was excited because I figured maybe she changed her mind. Guess what, she didnt. However I finally got closure. Even if this girl says no to you again you will need the closure. Otherwise it’s possible you may miss out on an amazing girl because in the back of your mind you are hoping she will reconsider. Don’t ask to early though. I think at least 6 months

    Either way good luck


    In regards to marrying someone “better” than oneself, I’ve always wondered about that.

    They say you should look for someone on a higher level than you, so that they will bring you up. But how does that work practically? Why would someone on a higher level than me want to marry me? Especially if they have the same advice, about marrying someone on a higher level than them? Thanks!

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