If the choice is mine, why ask God to keep me from sinning?
Look at what this blessing asks for. Make Your Torah our habit. Do not bring us to sin. Do not let the urge to do wrong rule us. Bend our urge to serve You. It can sound like asking God to make your decisions for you.
But the Gemara says that is the one thing He leaves alone. Rabbi Chanina teaches: "Everything is in the hands of Heaven except fear of Heaven." Rashi (the classic commentator on the Gemara) spells it out. Tall or short, rich or poor, smart or not: that is decided for you. Righteous or wicked is not. That was handed to the person.
Abudarham (a classic commentary on the prayers, written in Spain in the 1300s) raises this exact problem on our blessing and answers it in one line: "Even though good and bad are placed in a person's hands, he prays to God to help him do good and stay away from bad." The choice stays yours. The prayer is for help with it.
Why would you need help with your own choice? Rabbi Shimon ben Lakish says in the Gemara that a person's urge grows stronger against him every day, and that if God did not help him, he could not overcome it. Anyone who has decided at night to stop doing something, and then done it again the next afternoon, knows what he is describing.
The first request points the same way. The word is "targilenu," from the root for habit: make Your Torah our habit. Rav Kook (the first Chief Rabbi of the Land of Israel, who died in 1935) explains that a person's inner life moves fast, and only when Torah becomes a habit does life start to flow in that direction naturally.
So these sources see no contradiction. You choose. And every morning, before the day has thrown anything at you, you ask for help choosing.
Berakhot 33b, with Rashi,Abudarham, Morning Blessings,Sukkah 52b,Rav Kook, Olat Re'iyahWhy ask not to be tested? Isn't a test how you prove yourself?
One of the requests here is "do not bring us to a test." That can sound weak. If you believe in something, should you not want the chance to show it?
King David thought so. The Gemara tells that he asked God why people say "God of Avraham, God of Yitzchak and God of Yaakov" but not "God of David." God answered: they were tested by Me, and you were not. David said: "Test me." God agreed, and even told him in advance what kind of test it would be. David failed. It is the story of Batsheva. Afterward, the Gemara has David wishing his mouth had been muzzled before he said those words.
Rav, one of the leading teachers in the Gemara, draws the conclusion: "A person should never bring himself to a test, because David, king of Israel, brought himself to a test and failed." If David could not be sure of himself, who can?
Abudarham (a classic commentary on the prayers, written in Spain in the 1300s) explains our line the same way: not to a test, "because maybe I will not be able to stand up to the test."
Rav Kook (the first Chief Rabbi of the Land of Israel, who died in 1935) describes what a test is. A person has worked out how to live well in the world he knows. Then he suddenly finds himself in a new situation, a new environment, facing currents he never imagined would come at him. The request, he writes, is that no surprise should hit us that we have no time or way to adjust to.
None of this means tests never come. The Mishnah says Avraham was tested ten times and stood firm in all of them. The Gemara's warning is about going looking for one. The blessing goes one step further and asks to be spared.
Sanhedrin 107a,Abudarham, Morning Blessings,Rav Kook, Olat Re'iyah,Pirkei Avot 5:3Does it really matter who I hang out with?
The blessing asks God to keep us far from two kinds of people: a bad person and a bad friend. In the Gemara's wording it also asks for the opposite: "attach me to a good friend." (Our siddur has "good deeds" in that spot.) Of everything a person could ask for in the morning, the people around you made the list.
Pirkei Avot (the part of the Mishnah that collects the sayings of the early rabbis on how to live) shows how seriously this was taken. Rabban Yochanan ben Zakkai, the leading rabbi at the time the Second Temple was destroyed, sent his five students to find the right path for a person to hold on to. Rabbi Yehoshua answered: a good friend. Then their teacher asked which path a person should stay far from. Rabbi Yehoshua answered: a bad friend. (Rabban Yochanan preferred another student's answer, "a good heart," because he said it includes all the others.)
The Rambam (Maimonides, who died in 1204) states it as a fact about human beings: a person is made in such a way that his character and his actions are pulled after his friends, and he behaves the way the people where he lives behave. He is not describing weak people. He is describing people.
So what is the difference between a "bad person" and a "bad friend"? Rav Kook (the first Chief Rabbi of the Land of Israel, who died in 1935) explains. Some people do harm to everyone they meet. That is a bad person. But there are also good people who, when they are put together with one particular person, have something bad brought out in them. Neither one has to be bad on his own. As he puts it, someone can be "not a bad person" and still be a bad friend.
On that reading, the request about a bad friend does not ask you to decide who is a good person. The question it leaves you with is smaller: what happens to me around them?
Berakhot 60b,Pirkei Avot 2:8-9,Rambam, Laws of Character Traits 6:1,Rav Kook, Olat Re'iyah