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Which one is correct?

  1. I can't stand it when I lose things.

  2. I can't stand when I lose things.

I have come across the case when "it" is possible but I still doubt which of the above is correct.

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    Well, of course you can't stand if what you lost were your legs. :) – F.E. Dec 27 '14 at 9:36
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    It seems that the usage of "stand" that you want is one that needs a direct object. Consider: "I can't stand my brother when he pokes fun at me", "I can't stand happy people", "I can't stand rainy days", "I can't stand school". So, it seems that if a direct object isn't there, then the pronoun "it" is inserted to fulfill that syntactic requirement. That is, the sense of "stand" that is being used is a transitive one, and it needs an object. If the object (e.g. "it") isn't there, then your sentence could be misinterpreted--which is the problem with your 2nd version. – F.E. Dec 27 '14 at 10:12
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    You can find this usage in dictionaries. For example: to endure the presence or personality of <can't stand the boss>. – F.E. Dec 27 '14 at 10:15
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    @DamkerngT. Consider: "I can't stand my brother when he pokes fun at me" with "I can't stand it when my brother pokes fun at me" which uses a dummy "it". – F.E. Jan 9 '15 at 5:37
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    @F.E. Agree. I would prefer the dummy it, too. This question just made me curious if the when clause could take the place of it. As it turns out, it seems like it can't. Thanks. By the way, (a belated) Happy New Year! – Damkerng T. Jan 9 '15 at 5:42
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You probably want the first one:

I can't stand it when I lose things.

The two sentences have a very different meaning. The first means that losing things aggravates you. The second means that you can't physically stand (on your own feet) when you lose something, which is a very unlikely sentence.

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As F.E. points out in a comment, this meaning of "stand" sounds most natural when it takes an object. Thus, the following two sentences sound natural:

I can't stand it when I lose things.

I can't stand losing things.

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