“My Boyfriend Hasn’t Paid His Taxes in Ten Years. Can We Still Have a Future Together?”

My boyfriend “Karl” and I have been in a relationship for two years and are both in our early 50s. We have a very loving, fun, and compatible relationship, but there is one thing that is creating resentment for me. Some background on me: I’m an educated, professional woman with financial discipline. I own my own home and car, and I have a good retirement setup for myself because I’ve always lived within my means and make sensible purchases. My parents taught me well about managing money and paying what is owed. Karl is not like me in this regard.

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 a criminal, he’s 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?

Look, I can appreciate that the dating pool of a well-educated, professional woman in her 50s is different from what mine was when I was single and dating in my 20s. I understand that you have to make some compromises in exchange for companionship and affection. But I still think you’ve set the bar too low. What do you think? Maybe you disagree. 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 wendy(AT)dearwendy.com.


  1. 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.

  2. 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.

  3. “The food here is terrible and the portions are too small”

  4. “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.”

      1. Way harsh, Tai

  5. Bittergaymark says:

    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.

    1. So, how does it feel to be famous?

      1. Bittergaymark says:

        Amazing! Only Pedro Pascal still won’t return my calls.

      2. Avatar photo Guy Friday says:

        He won’t return your calls? He won’t return my toothbrush! 🙂

      3. Bittergaymark says:

        Um, when you get it back. Can I have it. Pedro…. Swoon.

    2. Bittergaymark says:

      Clarification: I am well aware, LW… that not everything on that list has happened. Yet.

  6. 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.

    1. Letter writer says:

      Leslie. I agree 100%. Thank you for the great insight.

  7. This man is selfish and irresponsible. Why would you even want to commit to that?

  8. 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.

  9. LW — #1, never marry this guy. If ypu do, a lot of his debts will become your debts
    #2 — ask yourself what you gain by moving in together. If you are happy dating this guy while living apart, why take the risk of moving in together? So far your current situation seems to be working for you, although you expressed an awful lot of concerns — most associated with moving in together
    #3 — why do you think you can’t do better than this guy?

    1. LisforLeslie says:

      One risk is that she has to clean up after a baby who clearly can’t manage to keep track of his stuff. I’m sorry, I am still having conniptions about spending $500 a week at walmart including buying new tools. New tools!

  10. Is this the person who wrote into the forums about 400 times about this guy, who also stole money from his mom? And your grown kids don’t like him? The answer is still don’t move in with him.

    1. LisforLeslie says:

      Oh man, I figured she didn’t have kids because they weren’t mentioned. If you move this baby-man into your home and you end up going through your retirement accounts, don’t assume your kids are going to take care of you when you run out of money.

      Old age is pricey. A comfortable old age is really pricey.

  11. 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.

  12. Excellent response and advice from Wendy. She nailed it exactly with this: “he is a criminal”. How many well established and moral women ( or man, anybody) long for a relationship with a guy who lives on the edge or further, of the law, and responsible societal actions? You can do much better and be much happier in time. I bet you won’t even realize how stressful and draining this is for you, until you are on your own or with a “real” man.

  13. Passingby says:

    “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.

  14. Letter writer says:

    Thank you all, your advice is spot on.
    No I wasn’t the person who wrote in 400 times. I don’t have children and he has 2. We are very compatible with a lot in common and can talk for hours and laugh.

    I went from seeing him at his house 4-5x a week to 1x a week in the last 3 months. He’s sensing something and keeps talking about when I’m going to move in with HIM. Not happening. Ever. I can’t live that way. Then I thought we could just live separately, not marry or put anything into both our names. What’s the point of growing old together like that. I was wondering if a person could resolve these financial troubles, but he’s 55.

    I guess I needed to hear it plainly, I deserve a more responsible partner. I feel sorry for him, it’s self induced drama and a character deficit how he manages money. Thanks again.

    1. I think your relationship is already over. Before I broke up with my former boyfriend for good, I was only seeing him once a week. It was definitely avoidance. Relationships are supposed to progress, not regress, in the first few years. If you’ve gone from seeing each other multiple times a week to once, stick a fork in it, it’s done. This guy is not relationship material, and if you were really having that much fun you’d be seeing him more.

    2. Carrotstick21 says:

      I’m really glad to see this update. I had one of the “cleanest” divorces that someone can have – no kids, no major contentions between us over assets because they were all mine originally when we married. I was reasonably good with money; he was lazy and selfish and unable to plan, sort of like your guy. And I cannot begin to stress to you how unbelievably expensive it was to unravel that marriage, and how many years of financial damage it caused to my life (I’ll have to get back to you when I can finally go a year without it costing me money, even now years later after divorce.) There is something especially galling about having to pay somebody to leave you. Please do not marry this man. If my experience can prevent someone else from going down that road, that would be something.

      1. Good point, when I got divorced in my 20s, my dad basically paid him off and fixed my financial situation. If he hadn’t, I don’t even know. And shout-out to my dad for quietly doing that and never saying I told you so.

    3. LW – I really do understand your situation and feel for you. You are seeking companionship and on a surface level he seems to fit, but underneath that is someone who has a substantial fatal flaw.. one that will seep into your life and begin to affect you the longer you stay with him. That lifestyle is indicative of a very irresponsible and quite possibly a sociopathic man (i.e. lack of any guilt, agency, empathy). I’m willing to bet he has very few or no friends, am I correct? Watch your stuff closely, don’t let him know how much you have and where, etc. I was married to this person for 17 years. I finally reached the point of no return and divorced him, while having to claim bankruptcy. He pilfered all of my retirement money unbeknownst to me as well. I had to start over in my 40s from scratch. I wish you well and please love yourself enough to heed these signs and warnings. I assure you money isn’t probably the only thing he plays crooked with. Best wishes!

  15. 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.

  16. 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.

  17. Prognosti-gator says:

    “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?

    1. Letter writer says:

      Thank you Gator and Carrotstick, your responses are sobering. You’re right, I AM insulated from his BS money issues. I’d go home once I became drained from thinking/ listening/ dealing with his shitshow. I just couldn’t figure out why he didn’t want to make his life easier and less stressful and drama filled. (Geez, he lost his wallet twice in two years and had to replace everything, once a week he turns the house into a crime scene when he can’t find his truck fob)

      His 85 year old father comes over and mows the lawn for him. The nanny/babysitters do the kids’ homework with them, all the laundry, and make meals for kids during the week while he’s at work, and clean up kitchen and bathroom. (their mother died 7 years ago). He has less housework and chores than I do and I live alone! But he always says he’s too BUSY to get his financials straightened out.

      Thank you again for the great insight all. I’ve gone from feeling sorry for him to seeing what he is. Will stick a fork in it this weekend, which will suck because I’ve already tried to break it off twice, but I’m more clear on it now.

      1. PassingBy says:

        Please remember that all you need to do is tell him that it’s over. You don’t need to convince him that it’s over, and he doesn’t have to agree.

      2. I’m glad that the rose-colored glasses are finally off, but I really really want you to think about why you left them on so long. This is truly a man who can not take care of himself. Your alarm bells should have been ringing much earlier.

      3. “His 85 year old father comes over and mows the lawn for him.”


      4. Good for you. Sometimes all it takes is telling it like it is and seeing what others think.Looking at it yourself written out or spoken out loud. That can be a helpline, or a therapist , or something like here.

      5. It only takes one person to end a relationship. Do it by text if that’s what it takes. Then block him. I’m serious. He obviously has no sense of boundaries, so look after yourself.

      6. LW, please check back in and tell us how it went and how you’re doing. I know it will be hard but I hope you’ll feel a weight off and actually feel better in a lot of ways pretty soon.

      7. anon4this says:

        When I broke up with a guy like this, I blocked him everywhere before I went to his house to do it. The only thing I’d left unblocked was text in case there was a snafu in reaching him (big city, lots of potential traffic issues). Google how to block him everywhere: social media, email, phones, etc. Then rip off the band aid. He won’t want you to go. He will probably cry and plead. Let him be someone else’s mess to care for. I always wonder what happens to these people in the end, but I’d never stay to find out.

  18. For what it’s worth Wendy, I’ve been reading your site for years and always found your guidance very balanced — just the right amount of tough love and kindness. Occasionally the message boards get harsh with a pile-on effect, but I think most people mean well.

    1. Appreciate that, thanks. And I agree – most of us really mean well!

  19. Canadian Gal says:

    I have been reading this site for several years, and I think while there has been a frank and fearless aspect of the advice it was playful and also had an empowering element to it: reach higher, you deserve better, you go this. There is something that I too noticed has changed in the past couple of years. To be honest the first time I noticed something that gave me pause about how a letter writer was addressed, was in letters shortly after Wendy shared a good friend of hers had died. I had just though perhaps it was grief. But there is something in the tone that has continued to change. I see it, and feel it here. I read a lot of advice columnists who have letter writers who are writing in from a perspective where they are completely and outrageously in the wrong about something, and yet the advice giver somehow is able to get them to reflect on their role in it, and is able to give them advice that when I read it looks like it engages in perspective taking, calling the reader on their behaviour, and yes at times taking them to task for it, but somehow isn’t harsh or mean. I can’t say with Wendy’s advice it’s this particular word, it’s this particular advice or letter, but it’s the overall tone that has started to shift. Here’s what I know about depression, it is not something that one day your are great, and the next day you are depressed. It is insidious, it sneaks up over you, over time. Over a couple of years, it’s hard to pin point, but then maybe you realize it’s there. I am not saying Wendy is depressed, but I am saying that frustration, exhaustion, depression, being overwhelmed can all effect tone. The reality is, when you are marketing a product and people are no longer interested (i.e. are not writing in), we can be defensive and rationalize or we can make a really difficult decision to critically look at why. There are numerous other advice columnist with children who no doubt were impacted by COVID, but still have people writing in for advice. This letter writer says something about your tone, and you get defensive and basically tell her well it’s obviously not that bad, because you wrote in. Maybe she wrote in because she knew you weren’t busy with fielding hundreds of letters like other advice columnists, and she thought even with the challenges she sees in the tone, she wanted to get an outside perspective. The irony is not lost on me that I will most likely get criticized for the tone of my post, but I am not trying to write comments for a living, and I welcome the comments!

    1. Even I, harshest critic on the planet, address someone’s potential depression with a little more tact, diplomacy, and kindness than this, Canadian Gal. If I may, can I suggest looking inward and asking yourself what you’re seeking in leaving a comment like this? What hole in yourself you’re attempting to fill?

    2. The person who writes something like this is a bored, empathy-lacking twat who spends way too much time online, and has some kind of pissy little grudge against a blogger who probably disagreed with her at some point.

    3. It would be really weird if having gone through fifteen years of life and particularly the last two, you wrote and gave advice the same way that you did in 2006.

    4. Letter writer says:

      @canadiangirl. Thank you for for trying to defend my perspective and offer reasoning for Wendy becoming more harsh and defensive. However, honestly, I think you’re taking it too far and your rationalization is a reach.

      I probably shouldn’t have provided that feedback because I did in fact write in. I have a right to feel that way, and people have a right to disagree. I have enough respect for Wendy and her people to respond helpfully to my situation, which they did.

      What I have learned in my life, regardless of message and manner, there is usually (not always) a kernel of truth in feedback received. It’s up to us to dig it out and think on it and maybe alter our behavior going forward, and that happens in the mind, not in written sparing words.

  20. anon4this says:

    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.

  21. Wendy, I think your advice is generally kind, honest, and to the point, what the rest of us get up to isn’t your responsibility. Years ago I wrote in to you with a question (with a different name) having found your site and lurking awhile to gain courage. I knew it wouldn’t be all sugar and spice. (It wasn’t, in the comments) and what it was, was helpful, your advice immeasurably so ; so I have stayed and learned a lot about human relationships and have tried to give useful advice in the few times I have anything of use to say. Thankyou for the work you do.

  22. Letter writer says:

    Update: I ended it over the weekend. That was draining! I was kind, sincere and tried to make it about me and not blame him. I should have expected his reaction due to standard operating procedure.

    He listened, and when I got done he launched into I can’t handle that he has responsibilities other than me, that my life is so much more simple than his, and just because he doesn’t run his life like I do it’s a problem for me, blah blah blah. When he finished his diatribe I asked him if he heard anything I had to say? In the end I “let” him dump me. I’ll be the bad and wrong person.

    When I left, I was sad of course because I really cared about him, but I felt so much lighter and woke up today with relief. Thanks all for your advice to help me see this was a dead end for me.

  23. Bittergaymark says:

    Seriously. Bravo!

  24. Well done you. It takes guts but so worth it, think your life will get so much better now.

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