Rabbi David Fohrman is one of my favorite speakers; I highly recommend his books. He was speaking on Pirkei Avos this past Shabbos, and I just had to tell it over. I've whittled down an hour-long speech into something much shorter, but hopefully all the details are in there.
א,ו יהושוע בן פרחיה וניתאי הארבלי קיבלו מהם. יהושוע בן פרחיה אומר, עשה לך רב, וקנה לך חבר; והוי דן את כל האדם לכף זכות.
א,ז ניתאי הארבלי אומר, הרחק משכן רע, ואל תתחבר לרשע; ואל תתייאש מן הפורענות.
Vov: "Make for yourself a rav" - Currently, there are only three beings superior to you in the world: One's parents and God. From amongst your peers, select an individual that you aspire to be like, to whom is your ideal. He doesn't necessarily have to be a rabbi; he is your mentor.
"Acquire for yourself a friend" - It sounds almost transactional; "buying" is an uncomfortable term in relationships. But many friendships are based on doing things for each other.
He brings an example if someone goes to car dealership, and the salesman offers you a coke. Don't take it! Why? Because you'll feel obligated to compensate him for that 35 cent soda in the form of a $35,000 car. Doing things for each other has no price tag in terms of equality; I help you, you help me.
These verbs, "make," "acquire," are very powerful, active terms, giving a lot of power to the individual. These two major relationships are the ones that anchor a person onto the straight and narrow.
"Judge everyone favorably" - This is how you treat everyone else besides your "anchoring" relationships; Pirkei Avos is not advocating restricting the social life to just these two. For everyone else in the world, the acquaintances, do not judge them. There is a Judge; that is Hashem. We don't play God by judging others.
If the rav or friend somehow fail in their ideal (such as being seen leaving McDonald's with a cheeseburger at 2 am), then a new rav is needed. One's aspiration cannot remain so if they are tarnished, since they are your ideal as a person. (I thought of this quote during the shiur: "Caesar's wife, like Caesar himself, must be above reproach.")
Zayin: "Distance yourself from a bad neighbor" - If someone questionable moves in, don't get too close.
"Do not befriend a rasha" - A rasha is a charismatic character who can easily suck people into his orbit. He is the anti-rav. He is the one who brings you down to the opposite of what you are trying to achieve.
"Do not depair of punishment" - Some people avoid the rasha and bad neighbor, yet see how they sin, and think, "Why haven't they been punished?" Just because they are not being hit by a bolt of lightning does not mean there is no Judge. Again: There is a Judge. It is just not you.
There are standards, there are rules. One should be aware of those rules. But not by judging others; that is not your job. There is judgment; but it is not done by you, and it will be done even if you cannot see it.
Torah, Avoda, and Gemilus Chassadim:
The Rav = Torah.
The Friend = Gemilus Chassadim.
Avodah = Hashem.
That is how one should relate to the world.
That is how one should relate to the world.