“My Boyfriend Doesn’t Spend His Money or Parent His Children the Right Way”

I am a 47-year-old divorced woman with an 18-year-old son. He is a high school senior and will be entering college next year. I support both of us. I have been dating “Frank,” a 51-year-old man, for 16 months. He has three children all living at home. He typically comes to my house every Friday and spends the weekends with me. His wife, the mother of his children, has been deceased two years now and Frank’s in-laws live within a block of his home.

Frank’s home needs a lot of work, such as a new kitchen and windows, so I sort of understand why he hasn’t invited me to stay at his house. He has never introduced his two oldest, both boys, to me, and I’ve met his youngest, a girl who is 16, only twice. However, since he is at my house during the weekends, he is around my son a lot.

Frank’s sons are 26 and 22 years of age. He says that they are supportive of his relationship with me but that trying to get everyone together to meet is difficult because we all work. According to my boyfriend, his oldest takes his laundry to his maternal grandmother’s house, and he had an opportunity to be an apprentice to a plumber but turned it down. His oldest has also been using his dad’s truck for almost a year now as he hasn’t gotten his own vehicle repaired. He does, however, have a job as a stock clerk at a local grocery store.

His second son has a job in a fast food restaurant. I’ve been told that the plan is for him to attend college. I also know that this son has had mental illness issues and is actively smoking marijuana. I have told Frank that I don’t feel the drug of choice for his depression is marijuana and that he should be in therapy and see a doctor. Frank disagrees with me as his son has been in therapy before and no therapist has ever given him any coping strategies. He also does not want him on medication. He does agree that he should stop smoking pot but doesn’t put an end to it.

I am writing to you because I’m confused with the situation and need advice. Frank is a very intelligent, loving man, but I think his sons might be taking advantage of him as he doesn’t set any rules and is enabling bad behavior. He does not make them pay rent and the second son usually has his friends at the house quite often. Frank’s plan is to buy a retirement home for us after his daughter is off to college. He is currently on a Disney trip with all three of his children at the moment (their 14th time to this place) and I’m spending this time re-thinking the relationship. I have made it known that I don’t agree with taking these expensive vacations when his house needs so much work, but he justifies it by saying that he makes a lot of money and does it for his kids. I do understand that he makes much more than I do, but I still don’t agree with it.

Thank you so much for any advice. — Re-Thinking This Relationship

It seems obvious to me that the reason Frank hasn’t introduced you to his sons and hasn’t integrated you into his life more is because he feels so much judgment already from you and doesn’t want to subject his family to that. His daughter was just 14 when she lost her mother, his sons only 20 and 24 — all such formative (and transformative) ages. Imagine shouldering such loss and grief at those ages — ages when society expects you to be moving forward at a rapid pace, figuring out what you want to do with your life and what steps you need to take to get there, all when the anchor that held you harbored and safe is suddenly yanked away. Throw mental illness struggles and hormonal shifts into the mix, and I can’t imagine the enormous reserve it’s taken for Frank to support his children and provide a loving safety net for them while managing his own grief. And here you are harping about how many times he’s taken his family to Disneyland?!

You literally have no say in how Frank spends his money or his time. You aren’t married to him; you haven’t even been invited to stay at his house!! And so what if his home “needs work”? Maybe for his family, creating memories on a fun vacation to a place that is familiar and probably reminds them of their mother is a higher priority right now than buying new kitchen cabinets or whatever. And who cares if his son does his laundry at his grandmother’s home? How wonderful that she lives so close to provide extra support and care. I can’t imagine the pain of losing a child like she did, but I bet having her grandchildren come to her home on a regular basis eases some of the grief. Maybe the laundry — what you likely see as something a 26-year-old should be doing somewhere besides his grandmother’s home — is an opportunity to connect with each other, to touch base, to express care.

So Frank’s younger son struggles with mental illness and has found something that seemingly helps manage symptoms, and you think it’s the “wrong drug of choice”? What gives you the expertise to make that presumption? You’ve never met the son. Have you even had any conversations with Frank about his son’s symptoms and the coping effect the marijuana has on him? Or do you just hear “marijuana” and immediately think it’s wrong? I happen to think it’s a fucking travesty that something that provides relief for millions of people who struggle with a host of issues continues to be stigmatized and lack universal legal protection despite having significantly fewer negative side effects than more typically-prescribed drugs (drugs that you would, no doubt, consider a “better choice” for this person you’ve never met before and whose symptoms you’ve never witnessed). I’ve seen marijuana work wonders for people who tried so many other coping strategies for their illnesses, and, even so, I would never decide it was the best choice for someone I didn’t know, whose experience I didn’t fully understand, and whose journey into managing their symptoms I wasn’t privy to. Where do you get off making these kinds of calls? The judgment — the moral superiority you’re showing — towards the way a family you don’t even know manages their grief, their illness, their transitions into new stages of life is somewhat stunning.

Yes, I think it’s right for you to be re-thinking your relationship with Frank — not because he isn’t perfect or because he spends his money on Disney trips instead of new windows and lets his son drive his truck and hasn’t kicked his children out of the house yet or made them get “real” jobs or give up coping strategies that you don’t approve of; you should re-think the relationship because it doesn’t sound like there’s a space in your heart for the life he lives, nor interest in making space. You want him to fit neatly into a life you imagine together rather than working with each other to flex and stretch into a real life.

Look, there’s mess in real life — old windows that need to be replaced and dead spouses to mourn and kids who don’t totally have their proverbial shit together. And there’s beauty and joy in that mess, too. And when you need a break from the mess, it’s nice to be able to escape for a bit to somewhere like “the most magical place on earth” (if that’s your jam)…and not be judged so harshly for it.


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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. dinoceros says:

    Frank is an adult who you are not married to, who has children who are not yours. He’s allowed to live his life how he chooses, run his home how he chooses, and parent how he chooses. He’s made it pretty clearly he’s not interested in your advice and you disagreeing with his choices is not going to make him choose something different. I don’t know if you’ve always felt that Frank does everything wrong or if it’s new. If it’s the former, then you probably shouldn’t have continued dating him once you found that out.

    I’m also not sure if you’ve always been the sort of person who thinks they are always right or tells others what to do. My assumption is maybe that you haven’t always been that way, but maybe raising a kid (and being used to being “in charge”) or your previous marriage made you that way. But you can’t really go into dating with that kind of judgmental, naggy attitude. He’s not your kid, and he’s not your husband of 20 years. You have to date people and treat them like your actual peer.

    Honestly, the whole part of him going to your house for the weekend when he has a teenager who lives at home is kind of weird (maybe that’s just me), and I’d agree that it probably comes down to the fact that he’s trying to keep you away from his kids and his home to cut down on how many times you tell him he’s wrong. I agree that you should probably just let him go. Then, you could find someone who does things you like better and he can find someone who accepts him as he is.

    1. I also thought it was weird that he spends entire weekends with he LW, leaving his teenage daughter at home. Unless she’s spending time with her grandparents?

      To me, that seems like a red flag.

      Everything else the LW mentioned. Yes to what everyone else said.

      1. dinoceros says:

        Even if she spends time with her grandparents, it just seems like it would send a not-great message if every weekend, you leave to stay at your girlfriend’s. There’s a difference between staying with grandparents often for visits and staying with them because your dad is going to be gone every weekend for the whole weekend. And your dad spends his weekends with someone else’s kid. When I was in high school, there was too much going on to spend much quality time with family on weeknights.

      2. I’m not arguing with you. I agreed. I think it’s weird and that’s one of the first things I noticed too.

        I only mentioned the grandparents because I hope he’s not leaving her with zero adult supervision. That would make the situation a lot worse.

      3. dinoceros says:

        I wasn’t arguing with you either. 🙂 Just adding to our “conversation.” Sorry if it seemed otherwise!

    2. This was one of the big things in the letter that stood out to me as well, and I guess I assumed that if the 22 and 26 year old brothers also live at home, they are probably providing the “adult supervision.”

  2. Bittergaymark says:

    Why do so many people expect those they date to magically transform and instantly start running their lives the way THEY (total fucking strangers) now see fit?
    Seriously. LW? Go fuck off.

  3. You judging him for spending his money on a family trip, rather than fixing up his house so he can sell it for more money and buy a nicer house for YOU to live in, screams “gold digger” to me. Unless the house is unsafe/uninhabitable, there is literally no other reason for you to care that he’s not fixing it up.

    1. Bittergaymark says:

      Seriously. SoTrue!

    2. House maintenance is important, sure. But all you said is that he has an old kitchen and old windows. Are the windows leaking? Is there rot around the windows that would lead to mold or other issues? Is the oven broken? Or is it simply out of fashion and old? If it’s old – WHO CARES? It’s not your house. Not your money. Just STOP. He’s an adult, who has been adulting a long time. He doesn’t need a mother.

      As for his kids – there is nothing you’ve said to lead me to believe he’s a bad parent. His kids are working. They are not in trouble. One smokes pot. Oh heavens to Betsy!

      You are looking for flaws. You have decided you know better and you don’t. You need to either shut up and never mention this again or you need to break up with him and find someone who is as judgmental as you are.

      1. Sue Jones says:


  4. ele4phant says:

    Wait…so you don’t live together yet, your finances aren’t entwined, you’ve been together just over a year? Lady – not your circus, not your monkeys. You need to back off here about not only dictating what your boyfriend does with his life and finances, but what his adult children do.

    Look, I think your fully entitled to look at Frank’s life and his entanglements with his children and think “Hmm, that’s a wagon I don’t want to hitch onto – I’m going to move on and find someone who I’d be more on the same page with”, BUT you have no grands to be inserting yourself into their lives the way you have been.

    You think his son should be in therapy and should stop smoking pot? Who cares what you think. He’s an adult, AND HE’S NOT EVEN YOUR KID.

    Back the f off.

    And, at least at this point, Frank can spend his money however he wants. If you don’t feel he’s behaving in a way that indicates he wants a future with you, well, then move on.

  5. Sue Jones says:

    So my house still has original 30 year old windows, and my husband hasn’t finished re-tiling the bathroom (and he likely never will) … but our son went to an expensive out of state arts camp this summer while we replaced a roof and gutters due to hail damage. We have invested in rooftop solar panels. My Prius now has hail dents all over it and is considered a “total” but it is in great shape mechanically so I kept the car and took the money. I bought myself new glasses with the money and saved the rest. We are planning going to the tropics this winter break with my husband’s family. I buy most of my clothes gently used on eBay these days. Some other woman obsessed with remodeling and image would have replaced the car already and we would have new windows, bathrooms, paint, flooring etc. But that woman isn’t me. I value education and travel and books over shiny stuff. I value being able to see with an updated glasses prescription over a new car with no hail dents in it. You should definitely break up with him, not because he is a bad or slovenly person, but you do not share values and that is huge.

  6. If my husband were to pass away and my kids and I were all struggling in our new normal, I think I’d hold on to my annual traditions, too.

    1. But I don’t think the letter writer is a bad human being for taking a closer look at what a future blending this family might really look like versus the story her boyfriend has told her about what it will be.

  7. ele4phant says:

    Totally missed that you haven’t even met his sons.

    How do you know that therapy is the right call and smoking weed isn’t? I assume you’re not a medical health professional, and even if you were, YOU HAVE NEVER MET THIS KID.

    It seems you have very strong opinions about the right way to live, and Frank isn’t on that path. Rather than try to force a middle aged man to change who he is, maybe just move on to someone who already shares the same values and perspectives on life as you do.

    You’re not compatible. Stop wasting each others time. You’re just going to keep frustrating one another.

  8. My gosh you come across horribly. Catch on that he hasn’t invited you to his home or introduced you to his children. It’s for good reason. You are a rude, judgemental person. He isn’t integrating you into his life for that very reason. Leave him so he can heal and be with a decent person.

  9. Avatar photo Skyblossom says:

    It sounds like the two of you have different priorities and values. There is nothing wrong with that. It just means the two of you don’t match and if there is too much differance that it can’t be bridge you need to realize that no matter how nice, or loving or kind or etc. he is that the two of you don’t match in critical ways. It is a good thing that you are taking time to evaluate the relationship and the priorities each of you bring into the relationship. It’s good that you look at the way you both parent and see whether you have enough common ground to share a home.

    I think that in general when you are dating someone whose grown children live with them and you’ve been dating for 16 months and they live nearby and you haven’t met those children that your relationship isn’t going to go anywhere. For whatever reason he has for not introducing you and his sons that reason means the two of you will never have more than you have right now. His sons aren’t going anywhere anytime soon so he comes as a package deal with grown sons who will live with him. If you will be happy long term with a boyfriend who will spend the weekends with you but the two of you won’t live together you are fine. If you want a future where the two of you combine your lives I don’t think you can realistically expect that to happen. If the two of you aren’t going to combine your lives then it doesn’t matter how different his priorities are from your own. If the two of you were to live together then it makes a huge difference and the two of you would have to be willing to talk about how you would manage your joint finances.

  10. All what you say, LW, is none of your business. He shouldn’t go on vacations with his children because his house needs work? Strange priorities.
    I agree with the golddigger vibe your letter sends. You start speaking of money (of course you support your 18 y.o. son!) and you end speaking of money. I guess he has less money than you think. So stop counting every dime he spends, because you won’t have a retirement insurance by him. His kids come first. You should move on and let him find a more openminded partner who accepts his family the way they are.

  11. Your parenting styles and priorities are so different (and incapatable) that I don’t see a happy future here. You’d be better off to move on, a marriage or even living together would just continually bring all the conflicts up and overwhelm the relationship.

  12. inkyboots says:

    Thank you for the comment about there being beauty in the messes of everyday life – I’m two years into a remodel (you really never know what you’ll find behind those walls) and I really needed to hear that. Even though our house is a little undone, I love it so much.

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