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Regarding Jews
1. Is a man permitted to woo the maiden (/her parents)? (Maybe it is not tznius (since maybe this is what a man does only to his wife))
2. Is it preferable that he (or family) do it ?
3. Or should he (and his family) just be himself and not do for her any special favors and let her want to marry him by herself?
4. Should he also inform of his negative traits (which he is not Halochikly obligated to)? (Or should he avoid them to speed up his marriage?)

If yes, please also give some practical advice as to how it can this be done.
It is By telling her how good he is, how he will take care of her, by giving her gifts, opening the door for her (what if you are not planning to open doors for her after marriage), paying for the food/drink?

Is over doing it, not good?
If yes what is over doing it?

(Sources that I know of, that Eliyezer gave Rifka a gift, Yakov cried that he could not give a gift to Rochel, Eliyezer showed Rifka's parents that her new husband is not poor and will be able to support her, Shchem told Dina nice words, (explaining how he can take care of her better then her father can)) A family might be similar to government (the husband is the ruler), and i see by government that the king/president many times tries to find faver in the people's eyes (this can be clearly seen in elections were people choose their leader (similar to when a wife chooses a husband))

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    Do you have any reason to think there is a way it should be done for everyone? The only people innovating it seems are those who make up rules when there are none – Double AA Jan 8 '17 at 18:29
  • some of the ideas are touched on here amazon.com/Jewish-Way-Love-Marriage/dp/0824604806 – rosends Jan 8 '17 at 19:00
  • This person is probably Protestant and believes that Jews read the Bible literally and try to use its stories as models for our lives in a direct, unmediated way. This is a Protestant way of using our texts, not a Jewish one so you have to start there before addressing the question. I would recommend a general book on how the shidduch system works. – SDK Jan 9 '17 at 4:03
  • @SDK why do you call me names? I think the Lubavicher Rebbe many times brings the Jewish idea that אין מקרא יוצא מידי פשוטו and מעשה אבות סימן לבנים. Regarding shiduchim as DOUBLEAA said above their are is not system with rules everyone does what they want, all I am doing is asking what is proper to do – hazoriz Jan 9 '17 at 9:56
  • @SDK my understanding is that by shiduchim usually the man or his parents pay for the drink/meal, so it seems he is anyway wooing her (giving her presents), to some degree – hazoriz Jan 9 '17 at 10:08
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+500

Rav Moshe Feinstein writes in his reponsa in Even Haezer 4:60, that the basic reason the Torah (and/or Rabbanan) prohibits closeness with a single "girlfriend" (hugging, kissing, and even inappropriate talking), is because it will lead to inappropriate closeness and attachment; which will lead to sin.

Shmos 22:15 "If a man seduces a virgin who is not betrothed and lies with her, he shall provide her with a marriage contract as a wife."

The Torah shows us that in an extreme case of a man "wooing" a girl to the ultimate extent of inappropriate closeness, the "punishment" is that he marry her. In other words: If you cause an act of commitment then you must commit!

We know that a man, in the natural course of seeking a wife, must of course interact with potential women. However, he should not do anything that will cause too much personal closeness, unless he already intends to be serious about marrying her (even then there are balanced limits).

1. Is a man permitted to woo the maiden (/her parents)?

Yes. A man should try his best to a) Be himself b) Show he is of good character c) Engage in as much talk and activity with a girl as is needed to decide if he wants her as his wife. d) Be a good salesman and show her and convince her of who he really is and that he likes her etc. --- provided that he only displays affections equal to his seriousness about her.

If he does express extra displays of affection, and then rejects the girl, he will probably hurt her heart and have caused inappropriate feelings of closeness between them.

So, on a first date, he will get to know her. He will display courtesy, manners and his own personality. He will not express his undying love. :)

As the relationship escalates. He certainly should tell her what he is truly feeling; namely, that he wants to get serious/ get married to her.

Therefore, saying things and giving gifts that would usually be taken as serious bonding attempts of a personal nature, need to be toned down or eliminated until he has decided he wants her as his wife.

For instance, taking her out for ice cream is fine. Giving her a bracelet is inappropriate. (even if not for the sake of kiddushin with witnesses)

I heard in Yeshivah, that the following deal was made for all time between Adam and Eve. They discussed, that in the future, if humankind would go out on dates; who should pay for dinner? Eve remembered that she was told she would give birth in pain. Adam was told that he would work hard for a living. So, they concluded: If the woman has to go through childbirth, the least the guys can do is pay for dinner. :)

Therefore, buying ice cream for her is a normal standard by which a guy shows he is a "mentch" and has class enough to pick up the tab. (manners, not intimacy). However, buying her a personal gift, would create an attachment that may make her think they owe each other something prematurely.

Comments are similarly judged. He does not say: "You look beautiful in that dress". He does say: "You have good taste in how you match your outfit." He does not say: "I think you are very attractive." He does say: "You have great energy this evening."

That is the dividing line between what wooing is acceptable and what is not. Be normal when scouting a relationship without acting prematurely.

2. Is it preferable that he (or family) do it?

The Torah tells us: Bereishis 29:26 "And Laban said, "It is not done so in our place to give the younger one before the firstborn."

Bereishis 18:8 tells us that the angels ate food when they visited Abrahahm.

Rashi explains: "and they ate: They appeared to be eating. From here we learn that a person should not deviate from custom. (see Gemara Baba Metziah 86b)

The answer to the question of how exactly one should choose to act in shidduchim, depends on the local custom. You need to ask Rabbis, neighbors, and friends, about what is acceptable and proper behavior in your local society. There is no set of Halachos that cover all possible details of these situations. Rather you should know your local custom. Some places have the girl meet in her home. Some want to go out on a date. Some talk on the phone first etc. In some places flowers may be accepted, in others it is not acceptable. etc. In some places, the parents have a lot of involvement before the couple meets. In others, it is up to the couple etc. Everything is according to the Jewish custom of that community and family.

3. Or should he (and his family) just be himself and not do for her any special favors and let her want to marry him by herself?

He should just be himself, while being his best self. He should do her favors, without doing her "special" favors. However, just standing there like a fire hydrant while she "decides" to marry him "by herself", is ridiculous. What girl would respect such a person? Communication must take place both ways so they both want to marry each other.

Yes he should open doors for her and act with manners and chivalry. If he doesn't plan on continuing this practice, then he should change his mind and continue to do so! :)

What is over doing it?

Bereishis 38:23 "So Judah said, "Let her take [them] for herself, lest we become a laughingstock. Behold, I sent this kid, but you did not find her."

In general, be discreet in matters of one's relationship with a woman. Do what you have to do, but not in a way that the matter causes embarrassment to her or to you (or the family etc.) .

4. Should he also inform of his negative traits (which he is not Halochikly obligated to)? (Or should he avoid them to speed up his marriage?)

He should of course ask his Rav advice on what issues he should and shouldn't reveal (even if he is not obligated to reveal them).

The Ben Ish Chai (Niflaim Ma'asecha 71) tells a story of a man who was very desperate, and broke into a widow's home to steal money. He regretted the act, and left her valuables on the table. The next morning, she awoke and went to the Rav to find her a shidduch since she needed a husband to protect her! The Rav suggested the nice young man who happened to (unbeknownst to anyone) be the burglar himself! (The moral of the story was that if you are destined to have money, you will receive it without having to steal it, etc.)

Rav Yitzchak Zilberstein asks if the chassan should honestly reveal to the kallah that he was the burglar?

He answers that he does not need to reveal it. He proves this from the Urim V'Tumim (Urim 28:3). A Bes Din, does not accept testimony from a biased witness because they cannot be sure the witness isn't twisting the story. However, if the witness has a bias against the defendant that the court is not aware of, he can still testify as long as the witness himself knows he is telling the truth. He need not admit his bias to the court. The burglar knows he sincerely repented in the middle of the act. Therefore, he is allowed to become the widow's husband without telling her he was the burglar.

I hope this helps. :)

  • +1 thank you, you do not give the possibility that "he wants to get serious" even before the first date, (if he is, is he "deviating from costom"?). Is "chivalry" Jewish? Is "opening doors for your wife" a Jewish costom (I guess in privet if you are trying to soduse your wife you should do it, but in public to do it seems wrong to me, I heard of a costom to stand on the kala's food under the huppa, and the Chabad version of it by the hosson walking in to the yihud room or the house first)? (The way I understand it is that respecting your wife more then yourself does not include serving her – hazoriz Jan 26 '17 at 12:12
  • I guess he can open doors for her not as a service but as a gift (you yourself say "be discreet", how is opening doors discreet?)) – hazoriz Jan 26 '17 at 12:13
  • (But if I remember correctly all the examples of seducing your wife are not by (serving) using your body (for example opaning doors), but by talking and giving gifts) – hazoriz Jan 26 '17 at 12:30
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    @hazoriz In general, R' Shlomo Zalman Auerbach writes (in his Shut Minchas Shlomo), that manners towards a woman in the street seems to be obligatory even towards married women (opening a door, helping her go in front of you onto the bus, etc.). (so it would seem even more important towards your date) Courtesy towards women is understood in most places as falling under "discreet". Doing laundry for her is service. Opening a door is manners. :) – David Kenner Jan 26 '17 at 21:42
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    @hazoriz btw, you probably don't want to use the word "seduce" in your sentence. It has a darker connotation. Also, no one is serious before the first date. :) – David Kenner Jan 26 '17 at 21:46
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In addition to the sources you mentioned, Rav Avigdor Miller, in his commentary on Bereishis, explains that the Almighty orchestrated the events by the well to ensure Yaakov would be able to exhibit his strength to Rachel (Bereishis 29:10). Moreover, Hashem beautified Chava for her marriage to Adam HaRishon as He braided her hair and surrounded her with light. Finally, the concept of tosefes kesuba, adding on more monetary value to the marriage contract, may also play a part in 'wooing' a wife.

Although it seems men take on the more active role in winning over a potential partner due to tznius constraints, women certainly strive to make themselves desirable as well, as the Mishna in Taanis (4:8) accounts how many women would tell their potential suitors to look at the family money or lineage in order to woo the men.

There is an important difference between being yourself and putting your best foot forward. Meaning, you might feel like schmoozing about a hobby you enjoy but realize you should be discussing valuable qualities when on a job interview. Does talking about your values and character traits mean you're not being yourself because you would ordinarily talk about sports or cooking (both are great outlets!)? Absolutely not. But when we date with the seriousness of marriage, we need to HONESTLY present ourselves as great as possible by focusing on our positives and what we can bring into a relationship. Sometimes other factors, like money or power, makes forming a relationship more enticing, although both are fleeting in contrast to the individual's qualities. Overdoing it would translate into offering a false sense of who you are. If a man truly wishes he could open the car door for his wife for as long as they live, then it's fair for him to do so during the courting stage when both aim to show their positive side.

  • +1, beautified Chava seems to be for the wedding not for the dating? He/they should avoid showing the negative (unless halochakli nessesery)? – hazoriz Jan 20 '17 at 8:05
  • Thank you for appreciating! Good point about Chava dating/wedding, since they were going to be married either way the extra beauty wasn't necessary--but still done to boost their admiration at the start. – NJM Jan 20 '17 at 12:25
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before the "date" happens there should be someone who knows the girl and someone who knows the bochur. This way before introducing them to each other it is clear they are on the same page concerning values. Then the "dates" simply become about each other seeing how the other is and considering if they liked spending time together. If that happens they can meet up a second time. After some time the bochur and the girl with guidence from their respective mashpi'im can figure out if they should marry. The dating part is mostly about getting used to being around the other person

you shouldn't be trying to woo anyone when you are looking to get married just get to know the person slightly better and see if your personalities match. If you go out of your way to be someone you are not while dating then realize she will get to know who you really are eventually anyways. Values etc should be known even before going out together. Also you are not marrying the person's family. It's important to respect her family but you don't need to "woo" them either besides simply being a mentch.

As far as giving gifts. It is best to avoid doing so until after the chuppah as giving a gift could be misconstrued as getting or being married.

  • ( +1) your last point , you are saying that even driving her, buying her water... Is forbidden? (I guess you consider something a gift if it is worth more then a pruta) – hazoriz Jan 23 '17 at 23:17
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here's something regarding honesty in business dealings from the Path of the Just ch.11, which I think also applies to selling oneself to a prospective wife:

There is a great distinction in the matter. For whatever is in order to show the prospective buyer the true value and beauty of the merchandise is good and upright. But anything which is to conceal its defects is fraud (Onaah) and forbidden. This is a general principle in faithful business dealings

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