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IRS doesn't catch everyone. But, people catch themselves. Doing things you got away with when single, or carefree can completely ruin your future life plans when there is a significant change - like meeting a spouse, wanting to get married, buy a home... And then, when that's extremely difficult suddenly the little IRS man shows up on your door to top it all off. Not to mention your state also...
A lot of people don't file returns, but have had wages taxed so that may not matter, although they could be screwing themselves if they would have got a refund...
If he's 1099, never figured out his taxes, he might have a small problem.
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