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What is the difference between pick and pick out when used in the sense of choosing? For example:

I will try to pick (out) the best place to live.

He picked (out) the righ career.

Dictionaries say that pick out means to choose something from a group. But doesn't pick mean the same? What does the out add to the meaning?

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My sense is that "pick out" means that the group is tangible and right in front of you (all the options are physically together) and that is a fairly objective choice.
- e.g., He picked out the tallest guy in the police line-up.
- e.g., He picked out the biggest piece of cake

When the choices are spread out or more abstract or subjective, I would never use out.
- e.g., He picked the best place to live (but had to go to different houses in different neighbourhoods on different days and then compare them. In addition, someone else might have chosen differently, based on their preferences, and also picked the best for their own situation.)
- e.g., He picked the right career (given his skills, temperament, and experiences, there were likely a few different jobs that he would be very good at, and he chose well to settle on one of these (rather than from among all the others), but it was not as simple as just picking an object - he had to study this, learn that, make these mistakes and have these experiences before he could become good at his career)
- e.g., She picked the tallest guy in the neighbourhood to date (even if true - did she check every guy - she did not line them up at one time and pick him out)
- e.g., He picked the best piece of cake (all the pieces were together, but it is his or your opinion, not necessarily shared by others)

Actually, I probably would alter the first case, but that's more a personal style - using out is correct
- e.g., He picked the tallest guy in the police line-up
- e.g., He picked the tallest guy out of the police line-up.
- e.g., He picked the biggest piece of cake (out of those remaining)

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The strictly defined difference is subtle. Both of these definitions come from Merriam-Webster.

Pick:

3 a : CHOOSE: SELECT
// tried to pick the shortest route


Pick out:

1 : DISCERN, MAKE OUT

For example:

I picked out my wife from among the crowd of people.


In short, if you are actually selecting something as a choice, then it is pick, but if you are noticing something as distinct from other things then it is pick out.

If you are being pedantic, you could say this:

I picked out [noticed] the man in the line up with a tattoo on his cheek, and picked [chose] him as the culprit.

Both refer to the same person, but the words are being used in a slightly different manner.

Having said that, most people don't make a distinction, and tend to use the words interchangeably.

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