“My Boyfriend Hasn’t Paid His Taxes in Ten Years”
Karl lives differently than I do; he doesn’t save money, doesn’t pay bills, and lives paycheck to paycheck, even though he wouldn’t have to if he’d manage his finances better. He hasn’t paid his taxes in 10 years, the IRS has been to his home, which also almost went into foreclosure a few years ago, and he doesn’t pay any of his medical bills because “health care is too much in this country.” He receives collection calls and mail daily. He spends a fortune at the grocery store unnecessarily (lots of expensive meats, cheeses, and produce, plus all brand name items, a third of which gets thrown away because he doesn’t use it up). He only pays his internet, mobile, and utility bills when he receives a disconnection notice, and he has the money to pay long before that happens! It’s like self-induced drama. I admit that he doesn’t blow money on drinking or gambling and he doesn’t spend much on clothes. But he still spends $500-$700 per week at Walmart. If he can’t find a tool in his crowded garage, he just buys another.
I make a lot more money than Karl does and I couldn’t even justify buying what he does. In all fairness, he doesn’t ask me to pay for any of his stuff, and if we go out for dinner, we take turns paying. He makes fun of me for contemplating purchases. We’ve talked about a future together. I’m starting to wonder if I can just watch this happen if we are living together. He doesn’t react well if I softly suggest the possibility of making better purchase decisions.
Can this be resolved by having completely separate financials? Or is this lack of discipline just the way it is? We were raised very differently when it comes to money. — Freaked out by His Walmart Spending
It’s often easier to hear from someone else that we need to do something we don’t want to do rather than have only ourselves to “blame” when we feel the inevitable discomfort of doing the thing we didn’t want to do but know is best for us. So, let me give you someone to blame for the heartache you’ll feel if/when you end your relationship: There probably is not a happy future in a relationship between you and a guy whose values differ so greatly from yours. This is more than his being irresponsible with money, which is something a lot of couples face and work through; your boyfriend is selfish and he evades contributing his share to the communal pot that allows our society to run smoothly. He’s immature and irresponsible, and he doesn’t seem to respect the boundaries you’ve set for yourself (making fun of you when you carefully consider spending money on something).
You’re better than this – than the promise of your relationship and the way you’ve sold yourself short – not because you make more money than Karl. You’re better than this because you’ve traded your scruples for someone whose redeeming qualities – if there are any – didn’t even warrant a mention in your letter. Yes, you say your relationship is loving, but you give no examples of Karl actually acting lovingly and you give no details of any of his positive traits at all. You didn’t even try to defend him against my potential attacks – which you must have been expecting – beyond saying that he doesn’t blow his money on drinking or gambling and that when you go out, you take turns paying. Yay?
Maybe the companionship and affection is worth whatever you give up in dating this guy. But don’t marry him! Don’t merge finances. Don’t move in with him. Don’t do anything that would complicate your ability to walk – run! – away from him as quickly as possible. Because I do think there will come a time when you’ll want to leave, even if you aren’t quite there yet. And you might need the voice of a harsh, critical bitch to blame for the potential heartache you might feel, so here I am. But I promise the heartache will pass quickly when you realize you’re better off without him. Because you are.
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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


This guy will ruin you financially if you move it together. Don’t ruin all your hard work. I can bet that as soon as you live together, those things he does will be so in front of your face you will regret it.
Well, this was an excellent response.
“the IRS has been to his home.” LW, I will repeat — “the IRS has been to his home.” I mean, good lord. That alone is hair-raising for any sane person, and what did he do with it? Learns nothing and mocks YOU for being responsible. Just …. wow.
“The food here is terrible and the portions are too small”
LOL!
“you are a mean and bad advice columnist who no one uses because you are too mean and bad. Please give me free advice. Thank you.”
That’s harsh.
Wtf?
If you promise to simply…
never live together
never combine finances
never loan him money
never resent paying for everything
never mind jailhouse visits
Well — then sure! You two can have one hell of a future.
LW – You and I are about the same age and seem to have similar views on financial responsibility.
Stay with Karl only if you want fun times and only if you do not marry, mix your finances or allow him to live with you. Keep him as a boyfriend. But he’s built a house of cards that, if you allow it, will topple you and ruin you financially.
There is no future, here. He’s had 50 years of poor money management. He’s not going to change how he saves/spends or his financial priorities at this point. You’re both going to get older and you’re going to want to retire and he’s not going to be able to because he has no money. You’re going to want to do things and he won’t be able to join you because he doesn’t have the funding, or you know that he’s putting it on credit that he can’t pay back.
And let’s say that he promises to cut back, to tighten his belt – do you really believe someone who is as disorganized and irresponsible will actually do the work and be OK with having less? The dude buys tools because he can’t find his? What the hell? You use a tool, you put it back. This is adult 101. I bet he’d last less than 1 week and he’d be right back buying steak instead of ground beef.
He is a scammer – absolutely. You know this. You can do better.
This man is selfish and irresponsible. Why would you even want to commit to that?
This is an unfortunate situation. I’ve been there, more than once…
Wendy is right, normal, healthy couples have money conflict. But we are talking about completely different fundamental approaches to money here. This isn’t something that can or will change, after 2 years he hasn’t learned anything and makes fun of her for being responsible. Maybe he’s jealous. If he has money but actively chooses to be irresponsible, that’s even worse than being ignorant. I didn’t know the IRS made home visits, scary.
Another point I’d like to make, just getting back into dating at 50, the dating pool IS thinner. I too have my financials together, but there are soooo many that don’t. I try not to be judgemental, but still isn’t a reason to sink my battleship because someone else didn’t bother. So LW, you are better and deserve better.
LW, never marry this guy. If ypu do, a lot of his debts will become your debts.
Some people are not very good at managing money – that is not your boyfriend. Some people strategically defraud others and keep creditors at bay – that is your boyfriend. His irresponsible and illegal behavior would be a dealbreaker for most. I think you are in denial of his moral turpitude, and naïve enough to believe his actions have no consequences.
“Can this be resolved by having completely separate financials? Or is this lack of discipline just the way it is?”
This lack of discipline is just the way it is. Separate financials won’t solve the lack of discipline. It will just stop it from draining your own money.
And it would have to be completely separate. You can’t live with him, you can’t own a car together, if you go on vacation, buy separate tickets. You cannot let yourself be in a position where he owes money, but your name is on the debt. And you would have to learn to ignore his financial situation.
That sounds like a pretty tall order to me.
To begin with I was oh well, that’s the way he is, and then you mentioned how he trashes the world’s resources and you know what, why would you want to be with someone like that unless they were having mental health problems and actively seeking help? Which is what he ought to do.
The problem with just keeping him as a boyfriend is that this is not just about money. He refuses to grow up. He’s self-destructive. That will show up in many, many other areas, if it hasn’t already. No one can compartmentalize that level of dysfunction.
“We have a very loving, fun, and compatible relationship”
No, you actually DON’T have a compatible relationship. What you have is a relationship where you’re able to HIDE the incompatibility because you aren’t yet intertwined.
It’d be like being in a relationship with someone with a substance abuse problem, but thinking it isn’t a problem because they only abuse when they aren’t around you. That might work for now, but it isn’t something that you’ll be able to keep hiding as you move toward being closer.
In reality, he DOES have a substance abuse problem. The substance is money.
Right now, none of the negative ramifications hit you. But if you move in together, can you stay shielded? Who pays for the house? If he gets ill, will you just be able to sit and watch him weather it without treatment, or will you feel compelled to pay to alleviate his problems? Will you make sure he has zero ability to access YOUR accounts? Can you trust him to not use your money when he misplaces something and needs to buy another? If he gets in (more) trouble with the IRS, will you just be able to watch, or will you feel compelled to bail him out? What if he’s crying and pleading with you?
I think we’ve dated the same guy! I lasted a few months. I wrote to DW about him (for other reasons! Shriek!). If not, then mine has a twin. Yes, a twin, because it was $500 at Costco, then threw it all out because he ate out every day. The tools were the same, but different hardware chain. But if you swapped out stores for anonymity, then we dated the same guy. But *his* IRS visit was because he was illegally claiming a home office. It was illegal, but he did it anyway. Was shocked by the visit revealing his kids using it as a playroom.
Nah, different guy. Run! RUN! like your hair was on fire.
He’s not a suitable or compatible partner.
You’re old, lonely and scared you can’t find anyone else your attracted to, and are ignoring massive red flags in order to justify the bum who makes you feel attractive and gives you a little bit of attention.
Dump him, look for other men in you actual physical league and you’ll be happy and married.
Right now you’re splitting your dates out. abut if you move in with him you will be paying all the household expenses. You said he doesn’t pay them until they threaten to turn them off. How will that go once you.liev together? Oh. the responsible one will pay!