Parshat Breisheet
(כה) וַיִּהְיוּ שְׁנֵיהֶם עֲרוּמִּים הָאָדָם וְאִשְׁתּוֹ וְלֹא יִתְבֹּשָׁשׁוּ.
(25) And they were both naked, the man and his wife, and were not ashamed.
What questions or thoughts does equating nakedness with non-shame bring up for you?
Does this verse imply that being naked automatically should equate with shame?

According to Rashi:

but they were not ashamed: for they did not know the way of modesty, to distinguish between good and evil (Gen. Rabbah) (Targum Yerushalmi), and even though knowledge was granted him to call [all the creatures] names, he was not imbued with the evil inclination until he ate of the tree, and the evil inclination entered into him, and he knew the difference between good and evil (Gen. Rabbah) (Zohar, vol. 1, 36b; Mid. Tadshei 7).

ולא יתבוששו: שלא היו יודעים דרך צניעות להבחין בין טוב לרע, ואף על פי שנתנה בו דעה לקרות שמות, לא נתן בו יצר הרע עד אכלו מן העץ ונכנס בו יצר הרע וידע מה בין טוב לרע

So why weren't they ashamed (at that point of their existence and nakedness) according to Rashi?
Rochelle Holzkenner (a woman who contributed on Chabad.org regarding modesty) asks the following question,
"The obvious, albeit shocking, inference from this whole story is that being naked is ideal, and shame (rectified through clothing) is a consequence of their mistake. So . . . if they did the right thing, would we all be walking around nude?" and unashamed?
If this were the case how would life be different?
Is the idea of being naked all of the time your ideal?
Rochelle Holzkenner brings commentary from Sforno to help us understand the ideal of nakedness: “All of their actions and all of their limbs were used for the exclusive purpose of serving their Creator, and not for their personal pleasure at all—to the extent that the act of intimacy was similar to eating and drinking, and they viewed their reproductive organs in the same way that they viewed their mouths, their faces and their hands.”
(ו)...וַתִּקַּח מִפִּרְיוֹ וַתֹּאכַל וַתִּתֵּן גַּם לְאִישָׁהּ עִמָּהּ וַיֹּאכַל. (ז) וַתִּפָּקַחְנָה עֵינֵי שְׁנֵיהֶם וַיֵּדְעוּ כִּי עֵירֻמִּם הֵם וַיִּתְפְּרוּ עֲלֵה תְאֵנָה וַיַּעֲשׂוּ לָהֶם חֲגֹרֹת. (ח) וַיִּשְׁמְעוּ אֶת קוֹל יְהוָה אֱלֹהִים מִתְהַלֵּךְ בַּגָּן לְרוּחַ הַיּוֹם וַיִּתְחַבֵּא הָאָדָם וְאִשְׁתּוֹ מִפְּנֵי יְהוָה אֱלֹהִים בְּתוֹךְ עֵץ הַגָּן. (ט) וַיִּקְרָא יְהוָה אֱלֹהִים אֶל הָאָדָם וַיֹּאמֶר לוֹ אַיֶּכָּה. (י) וַיֹּאמֶר אֶת קֹלְךָ שָׁמַעְתִּי בַּגָּן וָאִירָא כִּי עֵירֹם אָנֹכִי וָאֵחָבֵא.
(6)... she took of the fruit thereof, and did eat; and she gave also unto her husband with her, and he did eat. (7) And the eyes of them both were opened, and they knew that they were naked;... (8) And they heard the voice of the LORD God walking in the garden;... and the man and his wife hid themselves from the presence of the LORD God amongst the trees of the garden. (9) And the LORD God...said unto him: ‘Where art thou?’ (10) And he said: ‘I heard Thy voice in the garden, and I was afraid, because I was naked; and I hid myself.’
Going back to the Rashi above it seems that:

nakedness = evil
not being naked = good

but what actually makes the nakedness evil?

Do you associate nakedness with shame? embarrassment? What is the difference between your nakedness and someone else's?
If you are embarrassed about being naked at what point in your life did you start being embarrassed?

Sforno's comment above implies that knowing that you are naked leads to using your body for personal pleasure and not for holy purposes.
When is there a connection between personal pleasure and holiness?
There are a few examples in the Tanach where being naked is connected to serving God:
(כד) וַיִּפְשַׁט גַּם הוּא בְּגָדָיו וַיִּתְנַבֵּא גַם הוּא לִפְנֵי שְׁמוּאֵל וַיִּפֹּל עָרֹם כָּל הַיּוֹם הַהוּא וְכָל הַלָּיְלָה עַל כֵּן יֹאמְרוּ הֲגַם שָׁאוּל בַּנְּבִיאִם.
(24) And he also stripped off his clothes, and he also prophesied before Samuel, and lay down naked all that day and all that night. Wherefore they say: ‘Is Saul also among the prophets?’
(ב) בָּעֵת הַהִיא דִּבֶּר יְהוָה בְּיַד יְשַׁעְיָהוּ בֶן אָמוֹץ לֵאמֹר לֵךְ וּפִתַּחְתָּ הַשַּׂק מֵעַל מָתְנֶיךָ וְנַעַלְךָ תַחֲלֹץ מֵעַל רַגְלֶיךָ וַיַּעַשׂ כֵּן הָלֹךְ עָרוֹם וְיָחֵף.
(2) at that time the LORD spoke by Isaiah the son of Amoz, saying: ‘Go, and loose the sackcloth from off thy loins, and put thy shoe from off thy foot.’ And he did so, walking naked and barefoot.
Why is it acceptable for the prophets to be naked while prophesizing? Why doesn't their nakedness lead to unholiness?
Is the following article about modern day prophets?:

Brown University is set to host a weeklong “nudity” event featuring nude student performances starting next Monday, Campus Reform has learned. The event, named “Nudity In the Upspace,” is a weeklong program which is set to feature nude body painting, nude yoga, nude theater, and nude cabaret.

“Love being naked?” asks the event’s official description. “Want to be naked more? Want to watch others perform naked? Want to step out of your comfort zone? Want to talk about nudity?”

The Facebook event page, also indicates that the six-day program will include a clothed event called “Stripping Privilege: Undressing the Isms” on Wednesday which will include discussion on “power, privilege, race, class, gender, ability, and other isms how they intersect with nudity, body image, nudity in relation to (de)sexuality, etc.”

A Friday event called “A Devised Piece of Nudity” will involve students sharing “personal testimonies, movement, reflections, and more nudity.”

The event, which is being held for the second year in a row, does not require students to come in the nude and proclaims itself a “safe space” where they want to “reach out to as many communities at Brown as possible.”

According to the event page, cellphones, cameras, and bags are not allowed during any of the scheduled events.

Can Nudity in the Upspace lead to holiness or is this just an excuse for "cocky" pushing of boundaries?