I understand that it is good for Jews to be humble and not boastful
But are there times that it is not good?
Specifically is it good to be humble (avoid boasting) before your woman (wife/date)? would it be good to boast?
Why you should boast since my being humble you are making it harder for her to respect you
source that this is not good to do boast to woman of others (it seems that to your woman it is good, since it will make her desire you)
שבט מוסר/טז Shevet Musar chapter 16
ואל תשבח עצמך בפני אשתו במדות טובות שיש בך, שמא תבא למאוס בבעלה ולחשוק בך. do not praise yourself before his (someone else's) wife with you good traits that you have, since it might cause her to be disgusted with her husband and desire you.
Why you should be humble.
I heard that it can bring to an ayen horah, by getting people to sin by being jealous.
Some might say that the posuk below is also regarding boasting (that it is not good to boast regarding worldly things (which in my poor understanding are the things women are usually interested in)) Yirmiyahu 9.22,3
כֹּה | אָמַר ה` אַל יִתְהַלֵּל חָכָם בְּחָכְמָתוֹ וְאַל יִתְהַלֵּל הַגִּבּוֹר בִּגְבוּרָתוֹ אַל יִתְהַלֵּל עָשִׁיר בְּעָשְׁרוֹ
22 Thus says the Lord: Let not the wise man exult in his wisdom, nor the strong man exult in his strength, nor the rich man exult in his riches.
כִּי אִם בְּזֹאת יִתְהַלֵּל הַמִּתְהַלֵּל הַשְׂכֵּל וְיָדֹעַ אוֹתִי כִּי אֲנִי ה' עֹשֶׂה חֶסֶד מִשְׁפָּט וּצְדָקָה בָּאָרֶץ כִּי בְאֵלֶּה חָפַצְתִּי נְאֻם ה'. 23. But let him that is exulted exult in this, that he understands and knows me, for I am the Lord Who practices kindness, justice and righteousness on the earth; for in these things I delight, says the Lord:.
(See this midrash where it seems to understand the posuk that a person should not exult himself by using his mouth as Shlomo hamelech, Dovid hamelech and Korach did)
Is it not that my boasting you are humbling yourself?
if you were so big you would not need to boast, and by boasting you are humbling yourself, putting yourself so low that you need to praise yourself