My sister is incredibly cheap, and it’s getting to the point where it’s hurtful. Over the holidays, I suggested that we pitch in with our brother to buy my mom a gift she really wanted (an Instant Pot), but my sister said no. Instead, she knitted my mom a crappy scarf that she’ll never wear. I could tell my mom wasn’t sure why the Instant Pot wasn’t from all of us. And not having my sister share the costs meant that both my brother and I spent more than we wanted. That’s fine — she’s our mom! — but I wish she would be more aware of how her cheapness affects others.
I wouldn’t be so upset if my sister really couldn’t afford to pitch in, but I know she can. She has a good corporate job and has no trouble paying for a personal trainer and a nice apartment. (And for what it’s worth, she definitely makes more money than I do.) She’s just really tightfisted about anything to do with other people. Our uncle died last year and she wouldn’t even contribute to sending flowers! Whenever we go out to eat, she makes awkward comments about how expensive the menu is and tries to itemize the check instead of splitting it.
Obviously we aren’t gathering together or going on family trips this year, but hopefully we will again someday, and I don’t want this hanging over our relationship. I also don’t want to be so angry at her, but if the pandemic has taught me anything, it’s that we should be grateful for what we have and generous with the people we care about. How can I talk to her about this? What do I say? And how can I be less annoyed with her in the future? This behavior truly enrages me sometimes.
People usually do rude things because they don’t know better, not because they want to be hurtful. (With some big exceptions, of course, but let’s give your sister the benefit of the doubt.) There are many possible reasons why your sister can’t bring herself to pitch in. She may have serious anxieties about money that make her uncomfortable spending on things outside her immediate budget. Or she might have financial issues that you don’t know about. Maybe material gifts aren’t her thing, or she’s rebelling against you and your brother making decisions all the time. Or she might genuinely be a selfish jerk! Hopefully not, but there’s only one way to find out the real answer: You have to talk to her.
To figure out the best way for you to approach this, I called Matt Lundquist, a New York–based therapist who has frequently worked with families and siblings. His first question was: How have you brought up this issue before? “Sometimes people feel like they’ve raised it, but really they’ve just dropped hints, raised their eyebrows, or made a comment,” he says. “When something’s not working, when you feel resentment and frustration, you have an obligation to find a kind but direct way of talking about it. It’s important to name a problem clearly.”
Alternatively, let’s say you have raised it. Multiple times, with emphasis! Obviously, something about your technique isn’t landing. Which isn’t to say this is your fault — but it is worth looking back at those conversations and thinking about how you could make them more fruitful going forward.
The good news is, practicing the art of thorny discussions will benefit you in multiple areas of your life. Any progress you make will also serve you in other future conflicts (financial or not) that you may have with family members, a partner, a boss, and so forth. Think of it as a muscle or skill that you’re developing, not just a one-off problem with your sister that you’re trying to fix.
So, here goes: With hard conversations, your guiding principle must be that you do not know the full story. “It’s important to push yourself to be open to the possibility that what you’re seeing might be based on incomplete information,” says Lundquist. “If you’re going to invite somebody to address a difficult topic, I think you have a moral obligation to err on the side of openness, humility, curiosity.”
The point is not to ignore your own feelings, but to help the other person (in this case, your sister) feel comfortable saying something that she might not know how to express very well, or that might make her feel ashamed or awkward. (If there’s one thing I’ve learned from years of talking to people about money, it’s that they are weird and neurotic about it, and they usually assume that they’re “doing it wrong.”) If you want her to be honest, you need to leave wiggle room for this kind of vulnerability. Give it a soft landing space, if you will.
You could try something like, “I’ve been thinking a lot about how we don’t always agree on how to spend money as a family. I know that sometimes when I’m upset with somebody, particularly somebody I’m close to, it can be hard to see their point of view. Can you help me see where you’re coming from? Is there a way that I’m being unfair to you? I’d really like to understand so that we can be more on the same page in the future.”
Lundquist recommends going so far as to practice this discussion with a friend. “Find someone who can be honest with you and give you feedback on your delivery,” he says. “You may think that your tone sounds neutral, but it’s easy for these conversations to come across as accusatory, especially when there might be some history of that in the relationship.” You could enlist your brother, too — he might have some insights on this dynamic that you haven’t considered.
Then, for the important part: Listen! Don’t be defensive. Your sister may be vague and unwilling to delve into things at first, particularly if she’s felt attacked in this regard in the past. Be patient. Try again. Prove that you really want to understand, as painstaking as it may be.
It is important to consider the worst-case scenario: That your sister might continue to disappoint you. I sincerely hope that this isn’t the case, and I know it can be baffling and painful when someone you want to be close to — who was raised in the same household — becomes a person you can’t understand. “Your challenge is to find a way of operating that’s grounded in the reality of what there is to work with,” says Lundquist. “What you really don’t want to do is hang out in this resentment. You may need to go through a kind of grief. It’s painful to come to terms with a relationship that isn’t what you thought it was or what you want it to be.”
Ideally, it won’t come to that. And chances are, by being open with your sister, you’ll pave the way for her to become more open with you and to be more conscious of your feelings around this topic. She probably won’t change her behavior entirely, and you will have to shift your expectations for her. But she may become more empathetic to the fact that you don’t want money to be a factor when you’re all together, and she may be open to finding solutions that work better than the current standoff.
For example, she might always be anxious splitting the check at restaurants, but if she knows that it makes you frustrated, then you can — together — come up with a way to avoid that fraught moment. (Maybe ask the waiter ahead of the meal for her to get a separate check, and then you and your brother split the rest down the middle, or whatever.) Ultimately, it’s not really about the check — it’s about both of you feeling respected and heard.
