The Gemara in Pesochim (49a) says: לעולם ימכור אדם כל מה שיש לו וישא בת תלמידי חכמים וישיא בתו לתלמיד חכם, משל לענבי הגפן בענבי הגפן – “A person should sell all he has, so that he can marry off his son to the daughter of a talmid chocham, and his daughter to a talmid chocham, this can be compared to the branch of a vine being mixed with the branch of another vine.”
The Maharsha asks, why a good shidduch is compared to a vine, as opposed to some other tree. See there for what he answers.
Another question is, we daven: עוד ישמע בערי יהודה קול ששון וקול שמחה קול חתן וקול כלה – “It shall be heard in the city of Yehudah, the voice of happiness, the voice of simcha, the voice of the chosson and the voice of the kallah”. The question is, to daven for the voice of happiness and the voice of simcha makes senses, but what are we davening for when we daven for קול חתן וקול כלה, do the chosson and kallah have some special voice?
After we put tefillin on each morning, we say: וארשתיך לי לעולם – “you shall be forever betrothed to me”. The Chasam Sofer already asks, why are we davening that we stay betrothed to the Ribbono Shel Olam. Betrothal is a short-term thing, surely, we want to move on to the nisuin [marriage], so what are we davening for?
Normally, when one gets married, he is very grateful to the Ribbono Shel Olam, and is extremely happy. It’s well known that the son of the Divrei Chaim (R’ Garelitz) once met a chosson during his week of sheva berachos, and the chosson was walking around as if he owned the world, so he said to him “I don’t belong to you, remove me from your list”. The truth is, this is the way it should be, and ideally the chosson should keep this up, and it should continue to increase. However, very often the longer one is married, the further removed he becomes from this simcha. With this idea, we can answer all the above questions.
Wine has a unique nature, one which can’t be found by any other liquids and foods. By all other foods, the older the food is, the worse the food becomes. Wine is an exception, and the older it becomes the better. Therefore, we bless the chosson and kallah, that just like by wine, the older it gets the better it becomes, similarly, we hope that the older the shidduch gets, the better the marriage becomes. We give them a berachah that they should continue to be happier and happier with each other, and life in general. That’s why we compare them to a vine, as opposed to some other tree.
This also helps answer our second question. When a chosson speaks to his kallah during the week of sheva berachos, or when he speaks to his shver [father-in-law], he speaks softly and pleasantly, and speaks with the utmost respect. However, as time goes on, and the week of sheva berachos starts to fade away, he can already be heard from the other room. Therefore, we daven that his voice should stay sweet and soft and last like this forever. This is what we are referring to when we say, קול חתן וקול כלה.
This also helps answer our third question. When we daven, וארשתיך לי לעולם , we are asking that we should be happy and content just like when a chosson and kallah get engaged. Just like at the beginning their simcha is fresh, we hope to have the same relationship with the Ribbono Shel Olam.
Some answer, that the reason a good shidduch is compared to a vine is because vines lean on one another, just like vines lean on each other, similarly, we hope that the chosson and kallah will follow in the ways of the Avos and Imohos and not search out new ways.
With this we can explain the Gemara in Berachos (6b). The Gemara writes: דהמשמח חתן רב נחמן בר יצחק אמר כאילו בנה אחת מחורבות ירושלים – “One who makes a chosson happy, says R’ Nachman bar Yitzchok, is as if he has rebuilt one of the destroyed buildings in Yerushalayim”. The question is, why doesn’t the Gemara say: כאילו בנה בית מפואר בירושלים – “it’s as if he built a beautiful new building in Yerushalayim”? The answer is, a chosson already has the foundations, he already has what he learnt from his father and ancestors, he merely continues to build on what is already built. (Madanay Asher)
