Truth: Lying is Wrong but is Fibbing Okay? or, How to Answer the Question: Does this Outfit Make Me Look Fat?
Do not lie!

(יג) ...לֹֽא־תַעֲנֶ֥ה בְרֵעֲךָ֖ עֵ֥ד שָֽׁקֶר׃ (ס)

(13) ...Thou shalt not bear false witness against thy neighbour.

(ז) מִדְּבַר־שֶׁ֖קֶר תִּרְחָ֑ק...

(7) Keep thee far from a false matter...

ור"ל אמר תיו סוף חותמו של הקב"ה דאמר רבי חנינא חותמו של הקב"ה אמת

Reish Lakish said: Tav is the conclusion (i.e. final letter) of the seal of the Holy One, Blessed is God, as R' Chanina said: The signet of the Holy One, Blessed is God, is the word "Truth."1

1 When a king approves of an enactment drawn up by his subjects, he applies his seal to it. Simlarly, the word emet (truth), is, as it were, God's seal of approval. Why did God choose this word? Because it begins with the first letter of the alphabet (alef), continues with the middle letter (mem), and ends with the final letter (tav), thus alluding to the verses Isaiah 44:6, "I am the first and I am the last, and other than Me there is no God, and Isaiah 41:4, "I, the Lord, who was first and will be with the last as well" (Rashi).

Well, maybe a small lie is okay...
(יב) וַתִּצְחַ֥ק שָׂרָ֖ה בְּקִרְבָּ֣הּ לֵאמֹ֑ר אַחֲרֵ֤י בְלֹתִי֙ הָֽיְתָה־לִּ֣י עֶדְנָ֔ה וַֽאדֹנִ֖י זָקֵֽן׃ (יג) וַיֹּ֥אמֶר יְהוָ֖ה אֶל־אַבְרָהָ֑ם לָ֣מָּה זֶּה֩ צָחֲקָ֨ה שָׂרָ֜ה לֵאמֹ֗ר הַאַ֥ף אֻמְנָ֛ם אֵלֵ֖ד וַאֲנִ֥י זָקַֽנְתִּי׃

(12) And Sarah laughed to herself, saying, Now that I am withered, am I to have enjoyment - with my husband so old?" (13) Then the Lord said to Abraham, "Why did Sarah laugh, saying, 'Shall I in truth bear a child, old as I am?'"

וא"ר אילעא משום רבי אלעזר בר' שמעון מותר לו לאדם לשנות בדבר השלום... דבי רבי ישמעאל תנא גדול השלום שאף הקדוש ברוך הוא שינה בו דמעיקרא כתיב (בראשית יח, יב) ואדוני זקן ולבסוף כתיב ואני זקנתי:

And R. Ilea said in the name of R. Eleazar the son of R. Simon: A person may edit what has been said for the sake of peace... The school of R. Yishmael taught: peace is so important that even God altered what was said for its sake! For at first, [Sarah says] “My husband is old” and afterwards, [when God repeats her words to Abraham] it says “I am old.” (Genesis 18:12)

,דאמר רב יהודה אמר שמואל, בהני תלת מילי עבידי רבנן דמשנו במלייהו, במסכת ובפוריא ובאושפיזא.

For Rav Yehudah said in the name of Shmuel: In only these three matters is it the practice of rabbis to deviate in their speech from the truth: in regard to knowledge of a tractate1, in regard to matters of the bed2, and in regard to hospitality3.

1 A rabbi, for the sake of modesty, is permitted to understate the true extent of his knowledge (Rashi). If however, someone is in need of instruction or tutelage, he should be forthcoming with his knowledge and not pretend ignorance (Tosafot).

2 One who was asked whether he engaged in conjugal relations is permitted to reply untruthfully. As a matter of decency, intimate matters should not be publicized. (Rashi)

3 When questioned about one's experiences as a guest, it is preferable to downplay the owner's hospitality and avoid giving a favorable report. This is so that a gracious host should not be deluged with undesirable guests, who would return repeatedly and ultimately exhaust the host's resources. (Rashi)

Yup, sometimes it's best to lie (if you have the right intention)

תנו רבנן,כיצד מרקדין לפני הכלה,בית שמאי אומרים כלה כמות שהיא ובית הלל אומרים,כלה נאה וחסודה,אמרו להן ב"ש לב"ה,הרי שהיתה חיגרת או סומא אומרי' לה כלה נאה וחסודה,והתורה אמרה (שמות כג, ז) מדבר שקר תרחק,אמרו להם ב"ה לב"ש,לדבריכם מי שלקח מקח רע מן השוק ישבחנו בעיניו או יגננו בעיניו,הוי אומר ישבחנו בעיניו,מכאן אמרו חכמים,לעולם תהא דעתו של אדם מעורבת עם הבריות.

The Rabbis taught in a Baraita: How do we dance before the bride? (What do we say / how do we praise her?) Beit Shammai say, "We praise the bride as she is."1 And Beit Hillel say, "In all cases we say that she is a beautiful and charming bride.2" Beit Shammai said to Beit Hillel, "If she was lame or blind, do we say about her that she is 'a beautiful and charming bride?'" Whereas the Torah said, “Keep away from a lie” (Exodus 23:7). Beit Hillel said to Beit Shammai, "According to your view, if someone made a bad purchase in the market, should one praise it in front of him (the purchaser) or denigrate it? Surely, you would say that one should praise it in front of him.3 We should therefore praise even a homely bride.4 From here (this statement of Beit Hillel) the sages said: One should always have a pleasing disposition in front of other people.5

1 That is, we praise her based on her actual beauty and stature (Rashi). If she has a blemish, we say nothing at all. Alternatively, we praise whatever fine quality she does have (Tosafot).

2 That is, there is a thread of grace drawn over her (Rashi).

3 It is a general principle that the maintenance of harmony and peaceful relations overrides the problems of speaking a falsehood (Ritva and Rashi). This rule refers to a case in which nothing will be gained by pointing out a problem with the purchase - it is an obvious defect that the buyer must not have minded when he bought it (Beit Aharon).

4 And being silent or offering very limited praise is an implied insult (Tosafot). Although it is a lie to say she is beautiful, the importance of harmony overrides this concern (Ritva).

5 One should always act towards a person in the manner in which the particular person prefers. And since the bride evidently found favor in the groom's eyes, we also praise her to him (Rashi).

Can I browse beyond my budget?

(י) כשם שאונאה במקח וממכר, כך אונאה בדברים. לא יאמר לו, בכמה חפץ זה. והוא אינו רוצה לקח.

(10) Just as there is wronging in buying and selling, so there is wronging with words. One should not say to [a merchant], "How much is this object?" if he does not want to buy it.

ר"י אומר אף לא יתלה עיניו על המקח בשעה שאין לו דמים

R. Yehudah says, "a person should not even eye merchandise when he does not have money to buy it."