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Lose me once and get rich.

Lose me again and get poor.

What am I?

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I think the answer is

A tooth

Lose me once and get rich.

In some countries when a child loses their baby teeth they get money from the tooth fairy.

Lose me again and get poor.

Losing a tooth in the same place a second time is not good and you can be poorer (figuratively) for it.

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    $\begingroup$ You got it! ^ ^ $\endgroup$ – risky mysteries Jul 21 '20 at 19:58
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    $\begingroup$ Or losing a tooth a second time can mean a large dentistry bill. $\endgroup$ – Ross Millikan Jul 22 '20 at 15:25
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Is it

A trick/trap?

Explanation

If you fall for a trick once, then you become wise to it. But, if you fall for the same trick again, then you were never wise to it.

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    $\begingroup$ Interesting, yet not the one. $\endgroup$ – risky mysteries Jul 21 '20 at 18:33
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Could it be:

Zeroes

Reasoning:

If all your bank accounts are 0's then you have no money, but if you lose those 0's then you must now have money and be rich :)

If you lose all those 0's you now have on the end of your bank account balance, then you are poor again. (Ex. 100000 --> 1)

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    $\begingroup$ Nice answer! But that is not what I have in mind. $\endgroup$ – risky mysteries Jul 21 '20 at 18:23
  • $\begingroup$ Wasn't sure if it was a stretch or not lol $\endgroup$ – Derager Jul 21 '20 at 18:28
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I thought it was

Inhibitions

Reason

Lose them and you can become free possibly to make your fortune.
However, once if you lose them when you are rich you can quickly lose everything.

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