“I Feel Guilty for Being Wealthier Than My Friends”

First of all, let me start by saying I know this is a non-problem to have, and I’d never discuss it with anyone in person because I’m not an idiot. I hope it isn’t offensive. But it’s something that has happened to me and if anyone else has experienced it, I’d find advice helpful.

My husband and I are normal professionals with normal jobs. For the past 30 years, we’ve lived frugally – we bought a very modest home, we rarely vacationed or ate at restaurants, we bought used cars, we didn’t keep balances on credit cards, and we always invested our spare money. That, combined undeniably with luck — we were never unemployed – means that now we find that we’re…wealthy.

Our kids just graduated from college, and now we’ve got that tuition part of the budget again, and we’re realizing that we can spend more on ourselves and still meet our goals. So we’ve leased nice cars and are updating our house, and we want to loosen up a bit as we’re nearing retirement. Part of my problem is guilt. I’m donating money to some good causes, but I can’t pay for friends without it being weird. And I worry about losing my sensitivity – just today I was about to suggest a friend meetup at an expensive coffee place when someone else suggested a park, and I realized they didn’t want to pay anything. When friends are worrying about saving for retirement and paying for their kids’ colleges, I’ve been able to help with good advice, but when they say they have nothing saved for retirement at age 50, I just feel sad and guilty that I do.

So I guess my question is, now that we’ve achieved our financial goals, how do I relax and enjoy it? Please don’t roast me; if I came across badly, it’s hopefully just because I am bad at explaining.— Newly Wealthy

Hey, congrats on getting the kids through college, working hard, being lucky, and saving enough money through your lives that you can now comfortably enjoy it. I think you’re right in that this is kind of a non-problem to have, though I appreciate how you might feel temporarily awkward with your friends if you think they don’t have as much money as you do. It may help you to accept that they don’t want your pity or your guilt and, in fact, may not be as sad or stressed or whatever as you think they are. Maybe while you were not going on vacations or eating in restaurants, they were. Maybe they had a thirty-year jump-start on enjoying life the way you plan to now? This is neither good nor bad, but a perspective to keep in mind. Perhaps some of what you are feeling now is pent up from years of denying yourself little comforts and treats, and the very people you now feel sad for might have had reason to feel sad for you all this time. Would you have wanted their sadness and their guilt? Or would you have felt that you were living your life the way you thought was best, and just because it was different from how others were living theirs didn’t make it sadder or worse or wrong?

Another thing to keep in perspective is that perhaps when your friends don’t want to do something – like go to a coffee shop – it isn’t because they don’t want to spend money. (I mean, let’s be honest, how much money are you really going to drop at a coffee shop, even if it’s an expensive one?) There are other reasons a person might suggest a park over a coffee shop. Maybe, during Delta Covid times, they prefer being outdoors. Maybe the coffee shop is too loud. Maybe they don’t even like coffee. Maybe it was a beautiful day and they wanted to be outside enjoying the weather. I wouldn’t necessarily jump to money as a reason someone might prefer doing something different than what you suggest. That said, I’d continue being sensitive to different budgets in your friend group and not suggest activities or places that are pricey. Stick with the kinds of activities and places you’ve always enjoyed with them. Your having more money to spend now shouldn’t change the kinds of things you do with your friends.

So, how can you and your spouse enjoy your newfound wealth? Well, in your letter you say: “we’re realizing that we can spend more on ourselves and still meet our goals,” so do just that! Spend money on yourselves! Go out for meals in nice restaurants together. Take those vacations you denied yourself all your adult life. Go away just the two of you or, if you really want to be generous, invite your now-adult children along if you enjoy their company. Splurge on lodging that’s a few steps above budget-level. If you’re concerned about making others feel bad, there’s no need to share pictures on social media or tell your friends about where you stay and the amenities you enjoy. Keep it to yourself. Enjoy the luxuries and comforts you can afford now without humble bragging about them.

You said you can’t pay for your friends without it being weird, so don’t. Have you ever paid for them before (or vice versa)? If that isn’t part of your friend group culture, it *would* be weird to introduce that now. But if you’ve taken turns in the past paying for each other, that doesn’t need to stop just because you find yourself with more money now. Continue paying for things that are within everyone’s budget so that when it’s their turn to reciprocate, they can cover the same quality comfortably in kind. Then, it doesn’t get weird. No need to feel “sad” or “guilty” or whatever.

Finally, one more thing to keep in perspective: Monetary wealth is just one aspect of a person or couple’s or family’s whole picture. It’s great to feel like you’re lucky and to feel grateful. But while you’re feeling sad for others who don’t have what you do, you might be ignoring everything else they have that fulfills them and makes them happy and gives their lives value. Good health, a meaningful career, a beautiful and bountiful garden, pets, children and grandchildren, and interesting travels are just some of the many things that might round out your friends’ lives. They don’t want your pity or your guilt. Pack that stuff away. Enjoy your money and enjoy your friends, but don’t feel like you need to enjoy the two together.

I met a wonderful woman 18 months ago and we started living together two months after we met. She’s 62 and I’m 53 so we didn’t expect this to happen, but it did and we love each other. Her 39-year-old son has been living with her for 12 years now, works overnights, and pays $400 a month in rent. He thinks that is too much. He works 30 hours a week and is a slob – his bathroom and bedroom are disgusting. He smokes weed all day and plays video games. He never goes anywhere with friends or has had a girlfriend for 12 years now. Her 25-year-son just moved home and doesn’t pay any rent even though he makes over 100k a year! Neither of them does any chores or helps around the house. Neither of them pitches in for food or household products. I feel they are taking advantage of her, but she says they’re not. They don’t even socialize with us and spend 90% of their lives in their rooms. Both kids’ rooms are so dirty that it makes the house smell. It’s so bad that I don’t even feel comfortable inviting our friends or family over to visit.

I say she is enabling this behavior and needs to kick them out, but it always ends up in a fight and I have to back down and stay quiet. I can’t take it any more. The worst part of this is that she and I have never had a night alone in the house! We have to go out of town if we want to be alone and have a romantic night in because they are ALWAYS HERE! And now the older kid wants to pay less rent since his younger brother is here and not paying anything, and I’m at my rope’s end with this! Please help! — Tired of Living with Slobs

There’s a pretty easy solution to this: Move out. Get your own place where you and your partner can enjoy privacy together and you can comfortably entertain your friends and family without worrying about a stinky, smelly home. Recognize that moving in together after two months was too fast in this case and you didn’t understand what you were getting yourself into. Now you know and you gotta get out. You’ve tried talking to your partner about how you feel and she shows zero interest in changing anything. Clearly, she is not as bothered by this situation as you are. Maybe she even likes it, who knows. But you don’t, and no one is forcing you to stay, so go. None of the other adults you live with is going to make the changes you need in order to feel comfortable in that home, and the longer you continue staying there, hoping they do, the more resentful you will get. If you want to save this relationship and your sanity, move out already!

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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. Ohhh the second letter. You can’t move in with an ESTABLISHED family and start making demands they change everything because you know better. Yes, it sounds like a nightmare but one you willingly walked into and you can also walk out! Oy.

  2. Karebear1813 says:

    Agree with WWS but to add – because you moved so fast you haven’t been able to take a step back and to see the red flags from this women. Grown children, esp. the grown men should not be living with their momma. There’s an unhealthy codependency thing going on here and a lack of boundaries, respect, etc. For a grown women not to be able to have sex comfortably in her own home because of her children is … rather odd. I’d also say there might be some mental illness within this family that would need professional help.

    But on the bright side for the 25yr old. Maybe he might need some time to save money for a down payment on a home .

  3. LW#1 — it sounds like you aren’t flaunting your wealth in your friends’ faces, so nothing to be guilty, about. Wendy’s suggestions are great. You can live your normal life with your friends and have lavish vacations apart. Sprucing up and even major remodels of a home you’ve lived in a long time is not something limited to the wealthy. Fairly normal for kids out of college and living on their own. Leasing a ‘nice’, I notice you didn’t say ‘luxury’ car, also isn’t a big deal. If asked, you can say you have passed the stage of scrimping to pay for your children’s college educations. If you both leased Mercedes sports cars, then yes it will stand out.

    For the guilt: you say ” I’m donating money to some good causes.” With Covid, times are tough for a lot of people in your community in worse shape than your friends, who by all indications are doing ok (although no retirement savings at age 50 is disturbing, if they are at roughly equivalent income level to your family). Give more to charity, until the guilt subsides. It’s needed more than ever.

    LW#2 — I think the red flag you ignored is now slapping you in the face. You and she aren’t the match you thought you were. The suggestion to move into your own place is a good one. That is a test. You may be able to make this relationship work by living separately. If not, then this red flag is your deal breaker and you need to MOA. Push comes to shove, she chooses her sons over you.

  4. Leasing a car is not a smart money move. I mean, do what you want, but “nearing retirement” means you still have to be strategic in your decisions.

    1. ele4phant says:

      I’d agree, but it sounds like they’ve been very thoughtful about their money for decades, hence why they are in the position they are. They have been strategic about their financial decisions for years.

      At a certain point, you can have splurges and spend some money in a way that brings you joy.

      If they are continuing most of their good fiscal habits overall but starting to enjoy spending a little more freely, they are probably fine.

      So yeah, go ahead and lease those nice cars. Yeah, it’s not the smartest money move, but, sometimes you just want that nice car and if it’s not compromising the overall picture, meh, go for that indulgence.

    2. Actually, in a few certain circumstances, a lease does make sense. While it’s axiomatic that the smart move is to buy a late-model reliable used car and drive it into the ground, (which I’ve done multiple times) I’ve actually done the math and got a low-mileage high residual value lease which allowed me to spend less than the repairs necessary on a car. I like to look at the total cost of ownership over x years, including gas, repairs, taxes, insurance, etc.

      The lease made financial sense on its own, and then the “splurge” part was not getting the base model. It was well, well within our budget.

    3. On occasion, it makes sense to lease. The husband and I looked into it when his 20-year old car was past its shelf life and was going to cost more than its worth to fix. He ran all sorts of numbers and leasing made more sense than buying, but what made even more sense for us, who live in a major urban area, is rideshare, the occasional Zipcar and of course walking and public transit.

      1. I have leased cars before, and so have my parents on occasion (and my dad’s extremely smart and disciplined with budgeting).

        It can make sense if you’re low-mileage, need something temporary, and certain other circumstances.

  5. LW1 here, thank you, that was super helpful. In general, I do know that friends don’t want to spend the money when decisions are made because they mention it, and I’m totally good with that because I’ve always been there too. And I’m just as happy walking in a park as I am at a coffee shop.

    I think the thing that’s most helpful with the guilt is the thought that they spread out the experiences, where we didn’t. My husband and I always saw our parents struggle to save for retirement and we didn’t want that worry, so we went in the other direction, which worked for us.

    Thanks again.

    1. Whether they “spread out the experiences” or simply didn’t save enough, or had personal struggles or whatever, doesn’t matter. Don’t even go there in your mind with “We did this, they did that.” Just focus on you, and making sure you have a solid plan to protect what you’ve saved, even if you live a really long time.

      1. Thank you for this. I’m not a risk taker (did I mention my profession is accounting?) and almost all of our savings is locked up in retirement funds. It’s really some of the money we were spending on our daughters’ tuition that has become a kind of new discretionary windfall.

      2. Just enjoy it! It’s ok to have extra disposable income. There have been times I had more, and times I had less. When I have more, I treat people to more things.

  6. LW1: As I said in the other thread – you worked for that money, you saved it. You earned it. It didn’t fall in your lap. You made choices through the years.

    My mom likes to say “Money turns most problems into inconveniences.” Sure, money can’t solve all of life’s problems but it sure can help if your car breaks down or the A/C goes on the fritz. So save a little, spend a little and do things that make you happy.

    LW2 – you moved in 2 months after you started dating. So you knew at least one son lived there and has been living there for 12 years. Why do you think he should move out now? I’m not saying that this situation is normal, I’m just asking why you think your presence makes any actual difference.

    Also, where is your home? How were you able to simply pick up and move? Are you renting your house? Did you put all of your stuff in storage? Why is your life so transient?

  7. Bittergaymark says:

    I have some thoughts on this. I am going through a similar experience. Only with me, it’s Health. Not Wealth…

    Many of my friends are going through a major health crisis. One has MS so bad she is in assisted living. At 49. Two others died…


    It makes one feel very guilty. More later. I have a set to rip apart. (90 Day Fiance Bares All.)

  8. looked up 90 day sounds interesting. having something others do not (wealth, health) is certainly a thing. When others lose something they value infinitely should it make you value it more? IDK. Good luck with the set enjoy the ripping.

    1. I hate it when I have to rip things up but I am a right lemon/potential hoarder with so so many huge props and crap it is unreal.

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