Jacob and Esav Kiss
וַיָּ֨רָץ עֵשָׂ֤ו לִקְרָאתוֹ֙ וַֽיְחַבְּקֵ֔הוּ וַיִּפֹּ֥ל עַל־צַוָּארָ֖ו וַׄיִּׄשָּׁׄקֵ֑ׄהׄוּׄ וַיִּבְכּֽוּ׃
Esau ran to greet him. He embraced him and, falling on his neck, he kissed him; and they wept.
וישקהו. נָקוּד עָלָיו; וְיֵשׁ חוֹלְקִין בַּדָּבָר הַזֶּה בַּבָּרַיְתָא דְּסִפְרֵי, יֵשׁ שֶׁדָּרְשׁוּ נְקֻדָּה זוֹ שֶׁלֹּא נְשָׁקוֹ בְּכָל לִבּוֹ, אָמַר רַבִּי שִׁמְעוֹן בֶּן יוֹחַאי, הֲלָכָה הִיא בְּיָדוּעַ שֶׁעֵשָׂו שׂוֹנֵא לְיַעֲקֹב, אֶלָּא שֶׁנִּכְמְרוּ רַחֲמָיו בְּאוֹתָהּ שָׁעָה וּנְשָׁקוֹ בְּכָל לִבּוֹ (ספרי במדבר):
וישקהו AND HE KISSED HIM — Dots are placed above the letters of this word, and a difference of opinion is expressed in the Baraitha of Sifré (בהעלותך) as to what these dots are intended to suggest: some explain the dotting as meaning that he did not kiss him with his whole heart, whereas R Simeon the son of Johai said: Is it not well-known that Esau hated Jacob? But at that moment his pity was really aroused and he kissed him with his whole heart. (Sifrei Bamidbar 69.2)
וַיָּרָץ עֵשָׂו לִקְרָאתוֹ וַיִּשָּׁקֵהוּ (בראשית לג, ד), נָקוּד עָלָיו, אָמַר רַבִּי שִׁמְעוֹן בֶּן אֶלְעָזָר בְּכָל מָקוֹם שֶׁאַתָּה מוֹצֵא הַכְּתָב רַבָּה עַל הַנְּקֻדָּה אַתָּה דוֹרֵשׁ אֶת הַכְּתָב, הַנְּקֻדָּה רַבָּה עַל הַכְּתָב אַתָּה דוֹרֵשׁ אֶת הַנְּקֻדָּה, כָּאן לֹא כְתָב רַבָּה עַל הַנְּקֻדָּה וְלֹא נְקֻדָּה רַבָּה עַל הַכְּתָב אֶלָא מְלַמֵּד שֶׁנִּכְמְרוּ רַחֲמָיו בְּאוֹתָהּ הַשָּׁעָה וּנְשָׁקוֹ בְּכָל לִבּוֹ. אָמַר לוֹ רַבִּי יַנַּאי אִם כֵּן לָמָּה נָקוּד עָלָיו, אֶלָּא מְלַמֵּד שֶׁלֹא בָּא לְנַשְּׁקוֹ אֶלָּא לְנָשְּׁכוֹ, וְנַעֲשָׂה צַוָּארוֹ שֶׁל אָבִינוּ יַעֲקֹב שֶׁל שַׁיִשׁ וְקָהוּ שִׁנָּיו שֶׁל אוֹתוֹ רָשָׁע, וּמַה תַּלְמוּד לוֹמַר וַיִּבְכּוּ, אֶלָּא זֶה בּוֹכֶה עַל צַוָּארוֹ וְזֶה בּוֹכֶה עַל שִׁנָּיו. רַבִּי אַבָּהוּ בְּשֵׁם רַבִּי יוֹחָנָן מַיְיתֵי לָהּ מִן הָכָא (שיר השירים ז, ה): צַוָּארֵךְ כְּמִגְדַּל הַשֵּׁן וגו'.
...Esau ran to greet him. [He embraced Jacob and, falling on his neck,] he kissed him; [and they wept.] (Gen. 33:4). [The word] 'kissed' is dotted [above each letter in the Torah's writing]. Rabbi Simeon ben Elazar said . . . it teaches that [Esau] felt compassion in that moment and kissed [Jacob] with all his heart. Rabbi Yannai said to him: If so, why is ['kissed'] dotted? On the contrary, it teaches that [Esau] came not to kiss [Jacob] but to bite him, but our ancestor Jacob's neck became like marble and that wicked man's teeth were blunted. Hence, 'and they wept' teaches that [Jacob] wept because of his neck and [Esau] wept because of his teeth.
וישקהו, נקוד עליו, בב"ר (שם) אמר ר"ש בן אלעזר בכל מקום שאתה מוצא כתב רבה על הנקודה אתה דורש את הכתב, נקודה רבה על הכתב אתה דורש את הנקודה. כאן לא הכתב רבה ולא הנקודה רבה, מלמד שנשקו בכל לבו. א"ר ינאי א"כ למה נקד עליו, אלא מלמד שלא בקש לנשקו אלא לנשכו ונעשה צוארו של יעקב של שיש ושניו של עשו של שעוה, זה בכה על צוארו וזה בכה על שניו:
וישקהו, the word has a dot on each of the letters. In Bereshit Rabbah 78,9 Rabbi Shimon ben Elazar says that everywhere where you find the dots do not cover each letter of the word underneath we give preference to the meaning of the text as is, without the dots. When there are more dots than letters, we give emphasis in our interpretation to the dots. In this instance, there are as many dots as there are letters in the word וישקהו, so that we understand that Esau kissed Esau sincerely with all his heart. To this Rabbi Yannai countered by asking that if this is indeed so, why bother to put any dots on the word if they do not affect the meaning? We therefore must interpret that originally Esau had intended to bite Yaakov’s neck feigning an embrace. G’d made his teeth as soft as wax and Yaakov’s neck as hard as ivory. ויבכו, one on account of his neck, the other on account of his teeth.
וישקהו ויבכו (בראשית לג, ד). הביא רש"י נקוד על וישקהו, וחולקין בדבר הזה בספרי, יש שדורשין נקודה זו לומר שלא נשקו בכל לבו. ורשב"י אמר שנשקו בכל לבו. מר אמר חדא, ומר אמר חדא ולא פליגי. כי עשו למטה הוא כסמאל כחו למעלה:
וישקהו ויבכו . Rashi quotes different opinions regarding the significance of the dots on the word וישקהו. Some sages in the Sifri believed that these dots are to alert us to the insincerity of the kiss by Esau, whereas Rabbi Shimon ben Yochai said (despite the fact that we have an ironclad rule that Esau hated and continues to hate Jacob), in this instance Esau's human emotions were stirred, and he kissed his brother Jacob wholeheartedly. I believe that both views are completely compatible with one another. We must view Esau here on earth as merely the counterpart of Samael in the Heavenly Regions.
הדרש על נקודות וישקהו. טוב הוא לעתיקי משדים כי על דרך הפשט לא חשב עשו לעשות רע לאחיו והעד ויבכו כאשר עשה יוסף עם אחיו
The midrashic interpretation of the dots on top of the word and he kissed him, וישקהו is good for those who have just been weaned, but according to the straightforward interpretation Esav did not plan to do evil to his brother. And the proof is [the word] ויבכו, and they cried, [which is also used in the context of the reunion between] Yosef and his brothers.
ויבכו. שניהם בכו. בא ללמד שגם יעקב נתעורר עליו לשעה זו אהבה לעשו וכן לדורות בשעה שזרע עשו מתעוררים ברוח טהרה להכיר את זרע ישראל ומעלתם אז גם אנחנו מתעוררים להכיר את עשו כי אחינו הוא וכמו שרבי הי׳ אוהב אמתי לאנטונינוס וכן הרבה:
They wept. At that moment love for Eisov awakened in Yaakov as well. Similarly, whenever Eisov’s descendants genuinely acknowledge Yisrael’s greatness, Yisrael reciprocates with feelings of brotherhood.

"AND ESAU RAN... AND HE EMBRACED HIM... AND HE KISSED HIM AND THEY WEPT': IS IT POSSIBLE TO BELIEVE ESAU’S KISS?

"And Esau ran to meet him... and kissed him": Do not read 'and he kissed him' (vayishakehu) but 'and he bit him' (vayinshachehu). (Pirkei Derabi Eliezer XXXVI).

"And he kissed him" - the word has dots above it. Should one suppose that this was a kiss of love? R. Shimon ben Elazar said: But were not all Esau's acts of hate at the beginning? - Except for this one, which was an act of love. (Avot Derabi Natan II)

The word "and they wept" is a sure sign that we have before us pure human emotion. A person may indeed kiss without his heart being in it, but we can rest on the assumption that the tears which burst forth at such moments come from the depths of the heart; this kiss and these tears show us that Esau too was a descendant of Abraham our father, and not just a savage hunter, for how else could he have attained the rank of a ruler in the development of mankind? The sword alone, mere physical force, do not make a person fit for such status. (From the commentary of R. Samson Raphael Hirsch on the Torah)

"And they wept" - Both of them wept. This teaches us that, at that moment, love for Esau stirred in Jacob too. And so it is down the generations: when the descendants of Esau are inspired by a pure spirit to recognize the descendants of Israel and their qualities, then we too are stimulated to recognize Esau, for he is our brother. Thus Rabbi Yehuda Hanassi truly loved the Emperor Antonius - and there are many more such examples.
(From the commentary "Haemek Davar" of R. Naphtali Zvi Yehuda Berlin, Hanatziv from Velozhin)

וירץ עשו נהפך לבו כמו רגע בהכנעותיו של יעקב כאמרם ז''ל שאחיהו השילוני קלל את ישראל בקנה הנכנע לכל הרוחות הן לו עשו כן בריוני בית שני לא היה נחרב בית מקדשנו כמו שהעיד רבי יוחנן בן זכאי באמרו (גטין פרק הנזקין) בריוני דבן לא שבקונן:
וירץ עשו, his attitude changed suddenly when he realised to what extent Yaakov had humbled himself before him. It is of great concern to us seeing that we live among the descendants of Esau, people who are arrogant, consider themselves invincible. Yaakov’s conduct vis a vis Esau teaches that the only way to escape the sword of Esau is through self degradation and gifts. This corresponds to what our sages taught us (Taanit 20) that the curses of the prophet Achiyah Hashiloni were more beneficial to the Jewish people than the blessing showered upon them by Bileam. Achiyah had cursed the Jewish people describing them as a reed which bends in all directions, a reference to someone demeaning himself rather than facing up to adversaries. (Kings I 14,15) If the Jewish people during the period of the second Temple had taken his advice to heart, the Temple would not have been destroyed. Rabbi Yochanan ben Zakkai testified to this when he said “if not for the militant extremists the Romans would not have destroyed the Temple.”