Q: My fiancé hasn’t filed taxes in ten years. Will filing married filing separately raise any red flags for him with IRS
A: If the two of you get married and if you file your tax return married filing jointly the IRS may or may not look to see if your spouse ever filed. There was a time when the chances of that happening were remote--compared to today. With the advent of high-tech data systems now being used everywhere, the IRS is able to search through millions of tax returns in a matter of minutes, looking for "red flags" like this.
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A: If you file married filing separately (which I recommend if he is still not paying enough in estimated tax payments) you will be required to list his social security number. There is a good chance that the IRS may look into whether or not he is filing a return.
The answer is for him to seek assistance with settling his tax issues. You should not stop filing as this may end up compounding the problem. Most of us offer a free consultation and would be happy to go over his options with him. Tell him to stay away from the places you see advertised on tv and contact a good tax attorney.
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