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If he got a 1099, then the paperwork is saying he's an independent contractor. That could be a big problem if no taxes have been withheld. There could be a huge tax liability owed by your boyfriend. Independent contractors have to pay all the various taxes and social security, etc.
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.
This is messy.
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