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Originally Posted by glatt
Did he fill out a W4 when he started working? Was there any paperwork involved when he started his job? The IRS will not be too happy with the boss if your BF filled out a W4 when he started, and no withholdings were made. But if that paperwork wasn't filled out, then the IRS will be looking at your boyfriend to come up with the taxes.
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It can get worse. If you're a contract worker, the IRS requires quarterly pre-payments on your expected tax liability unless you can reasonably show you didn't expect to have any tax liability based on previous returns. If they start scrutinizing the boyfriend, they could not only come up with a large amount of taxes they think he owes, they could also slap him with penalties for not paying it "on time" throughout 2010.
Leave the IRS out of it. He's quitting his job, he's got a better one... just walk away from it.