Dear Roe, Lately, I’ve found myself becoming increasingly irritated about money. I earn an okay wage, but certainly not as much as some of my friends and family members. Yet somehow, I often seem to be the one paying more. I’m noticing it more now because I’m trying to save and be more careful with money. Going out has become so expensive, and I’m realising how often I’m the one quietly covering more than my share. I’ve always considered myself a generous person and I enjoy treating people. I like buying rounds for the people I love. I like picking up the bill from time to time. I like finding a good gift for someone’s birthday or bringing decent wine and beers when I’m invited somewhere. If anything, I’ve probably erred on the side of being too generous over the years. What has started to bother me is how rarely other people seem to think the same way. There never seems to be a shortage of people willing to have another drink. There seems to be a shortage of people willing to buy it. Friends will ask me to get them a drink and tell me they’ll Revolut me. Sometimes they do. Sometimes they don’t. I know everyone has different priorities when it comes to money. People are entitled to spend their hard-earned cash however they like. But I find myself raising an eyebrow when friends who think nothing of regular salon appointments, expensive gym memberships or weekends away suddenly become remarkably reluctant when it’s their turn to get a round in. I don’t keep a spreadsheet and I’m not looking for everything to balance out perfectly. But I’d love, just once in a while, to hear someone else say, “I’ve got this one,” or, “Don’t worry, I’ll take care of it.” I’d love to be the person being treated occasionally. But I hate the idea of becoming someone who counts every penny. So how do I stop? How do I learn to sit through the awkward silence and let somebody else get the round for once? I had to cut down your letter a lot because it was long and full of examples and feeling, which shows how much this issue is bothering you. And that’s completely understandable – as you note, going out (and staying in, and everything else) is horrendously expensive these days. And when you have both savings and friendships that are being depleted by uneven dynamics around money and socialising, it’s time to address the issue.Conflicts over money are tricky, because of course money is never just money. Money is safety, it’s survival, it’s power, it’s care, it’s privilege, it’s stress, it’s opportunity, it can define what kind of future life is possible for us. It’s also a question of values and a code of behaviour, which is often inherited from our families or peers. We often assume that everyone shares our internal code around money, and when we discover they don’t it can feel like they’re breaking a rule, rather than simply making a different choice.Your letter suggests that you have a very clear code about reciprocity and fairness. If someone buys a drink, you buy the next one. If you’re invited over, you bring a gift. If someone pays, you pay them back. It’s a code that involves being mindful about turns and effort and equality. It’s a lovely code, I share it – but it’s not universal. Some people don’t think that way, or don’t think about money at all. Some people are inattentive. Some people have so much money they assume it all comes out even in the wash. And some people are just happy to let other people pay.What stands out to me about your letter is the conflict you’re experiencing, and how much it’s impacting your relationships. You don’t want to be a person who is anxious about money or keeping track of every bill, but because you’re overspending and under-receiving, you have become just that. And you’re now also obsessively noting the way your friends spend their money and are using these expenditures as evidence in a case against their character.This is what resentment does. And to be clear, I completely understand your feelings. But acknowledging how this dynamic is affecting you is important. This dynamic is making you unhappy and needs to change. And because you cannot change other people’s behaviour, you’re going to have to change your own.Resentment often grows when unspoken expectations repeatedly go unmet, and I suspect that’s exactly what’s happening here. You expect the people around you to notice whose turn it is, to care that you’re trying to save, to want to treat you occasionally because that’s what you would do. But they keep failing to meet those expectations, you continue not expressing them, and resentment grows.The pints aren’t the thing you value. You value friendships that feel reciprocal, caring and generous, so spend your money on those things insteadSo what do you do? You stop waiting for other people to start living by your internal code, and you create a new one for yourself. You don’t need to become mean or start a spreadsheet. But you do need to become much clearer about your boundaries. Remember that boundaries are not miserliness. Boundaries are what allow you to feel comfortable, respected, and resentment-free. Boundaries are what make genuine generosity feel possible, and good.Adopt some of your friends’ brazenness – not to avoid the bill, but to cheerfully, openly, unashamedly talk about money. Because here’s a tip: people who genuinely care about fairness in a relationship are rarely offended by conversations and boundaries around money. So practise announcing and enacting your boundaries. Sentences like: “I’m budgeting differently at the moment, so I’m just going to get my own tonight,” and, “I got the last round – do you mind grabbing this one?” are your new best friends. If someone asks you to pick something up, send the Revolut request immediately, not three days later after you’ve convinced yourself it’s awkward. You’re not chasing them, you’re just completing the transaction. If they don’t pay you back, retain that information. Next time they ask, say, “Oh I think you owe me for X, so how about you get this one so it’s even?” Or ask them to cover the upfront cost and pay them back immediately, so you’re not out of pocket. Keep it light, cheery, and matter-of-fact. Show them what feels obvious and natural to you. Make your code explicit.Most importantly, get clear on what you actually want your money to do. From your letter, focusing your generosity on rounds isn’t bringing the sense of openness and connection you’re seeking, nor is it respecting your personal financial goals. So invest in your savings and pension first. Think about midterm goals like holidays, bigger experiences. Put aside some money for thoughtful birthday presents and intentional spending, like bringing a nice bottle of wine to dinner or memorable experiences with people you love. The pints aren’t the thing you value. You value friendships that feel reciprocal, caring and generous, so spend your money on those things instead.Generosity only remains generous when it’s freely given. The moment it becomes something you feel compelled to offer and silently resent when it isn’t returned, it’s no longer generosity, it’s self-sacrifice – and that’s not serving you, your friendships, or your finances well. Invest in your boundaries. The advantages will rapidly accumulate.