Bad boy braggart

Tax cheating a character flaw?

My boyfriend brags about cheating on his taxes. I’m disappointed. I’m not worried about Uncle Sam as much as I am about me. I’m considering marrying my boyfriend, and I’m wondering if this is a red flag. Will he be dishonest in other ways? Will I end up getting financially wrapped up in this? When I tell him I don’t approve he laughs it off. Anyone else had this experience? -- Carla from LA

NuKazoo readers shared their experiences:

I knew before we got married that my wife wasn't current on her taxes.  I thought of it more as a result of her helping out her brother's family when they needed a loan than as "cheating" the IRS.  I figured that once we got married I'd pay the back taxes and square everything up with Uncle Sam.  After we cleared up the tax problem I realized the truth -- my wife was a compulsive spender.  The financial stress and her lying contributed to the breakup of our marriage.  Was cheating on taxes the problem?  No, it definitely was the spending.

-- Jim from Chestnut Hill, PA

In my experience, braggarts are often blowhards whose boasts reflect imagination more than fact.  Before having any emotion in response to a bragging tax evader, I'd get the facts.  It may just be that bravado makes him feel cooler than he believes he is. 

-- Cori, Potomac, MD

My husband brags about the ways he avoids paying taxes and I used to wonder about the integrity of the man I love. The fact is, though, that he has never for a moment been deceitful or unfair with me, our friends, or business associates.  I came to realize he values his personal integrity highly, but he thinks the government is a bunch of crooks.  He views the whole lot as a threat, just one step short of enemies. 

-- Amy in IN

Tax cheating may be the tip of the iceberg.  My sister dated a guy who cheated on his taxes and on her.  He cheated his customers, suppliers, and friends, to the extent that his buddies could be called that.  He had such well-crafted rationalizations that he was able to justify what he did to maintain a certain image.  His behavior may have been genetic or cultural.  Everyone in his family viewed rules as obstacles to get around in order to get what they wanted.  Beware!

-- Greg from MI

Be thankful he tells you about his tax cheating!  My experience is that what you don't know is what'll come back to bite you.

-- Gina in Barrington, IL

My fiancé used to brag about how clever he was at finding ways not to pay taxes. He treated it as a game and I didn’t give it much thought. I dismissed it as routine male BS. After we got married, though, it all caved in. The IRS treated me as though I were funding terrorists. When they found that I had some investments, they seemed to think that they had found buried treasure. They talked to my employer, tainting my reputation. I had to change jobs. We’re financially trashed, but still married and in counseling when the budget allows.

-- Kate from BOS

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