#227: Should I leave my financially insecure boyfriend?

Hey!

Welcome back to Dear Baby. Today I have two questions instead of three because my answers were too long to accommodate a third. The first is about whether new clothes can ever actually fix a problem and the second is about whether “financial incompatibility” is reason enough to end a relationship, the latter of which invited me to reflect a lot on my own. I found both of these questions interesting and difficult to answer, so I’m extra curious to read the comments today.

Two things before we start: GO ZOHRAN!!! God, what a high (so rare these days). Of course it was quickly diminished by the absurd rhetoric that’s followed his win, but I’m trying to hold onto optimism. Also, wildly unrelated but in case you missed it: I reviewed my baby registry on Wednesday. Who knew we all had so many feelings about strollers?

On whether clothes can fix a problem

“Hi Baby,

I am sure this question is as old as time, but I can’t find an answer to it that feels like it clicks. Will new clothes make me feel better about my body?

Over the past few years, as I left my twenties, I worked on body neutrality. This came after years of disordered behaviour with eating, exercise, and self-worth (or lack thereof). I also was really into style in my early adulthood and would thrift all the time, but with my mindset towards consumerism shifting, and frankly having a tighter financial situation these days, I have gotten much stricter with my shopping. Over the past year, and especially at the start of 2025, I really struggled with anxiety and depression, and often was just hanging on. Some days I ate as much of whatever was appealing because more often I couldn’t stomach food at all. Unsurprisingly, my body has adjusted to this fairly poorly. I knew that I felt off, but since my circumstances changed (I finished off a school-based practicum in May, now with a few months totally off to rest), I was ready to be patient and let things steady themselves out.

Cue the weather warming up. I quickly had to bring my summer clothes out of storage, and upon trying on my favourite pieces from years prior, incredibly few things felt right on me: tight, a little heavy, a little bunchy. To be clear, I don’t think they look that different, but I’m dreading getting dressed all the same. So back to my question: I’m doing a lot of mental gymnastics trying to figure out if my clothes are distracting me from living out a restful and joyful summer and whether I should buy/wear things that are comfortable, or if my desire to buy new clothes reflects my still-unresolved self image, fatphobia, anxiety, and depression. I do feel like I can be overly strict with myself when I want to shop, but when I weigh the sides of shopping to feel good, and not shopping to save money, vote with my dollar, be environmentally responsible, I end up justifying the self-policing.

So, to shop or not to shop? Do you think there’s another way?”

There is a pretty simple answer to this question which might actually be the most useful: You deserve clothes that fit you. And yes, I think tightness and bunching count as not fitting. No need to replace everything in a shopping spree that contradicts your values—I say buy a few staples that make your body feel respected, either secondhand or from thoughtful brands you trust. Sacrifice may be important in the long-term climate conversation, but I’m not sure forcing yourself to continue wearing clothes that make you uncomfortable is the right place to start.

All that said, I think there’s a lot more to this question than the matter of whether to shop. The pattern that stuck out to me most was your complicated relationship with pleasure and self-deprivation. You mention your disordered history with eating, exercise, and self-worth, which, if I may project, likely concerned disciplining pleasure-seeking behaviors like eating “junk food” or laying around all day, and in turn moralizing your ability to deprive yourself of those things.

I can see you’re actively working on winding down this value system. In the throes of anxiety and depression, you let yourself cope however necessary. And when you came out of that place, rather than reflexively countering your laxity with discipline, you were prepared to be patient with yourself and “let things steady themselves out,” which I think is a very loving and realistic approach to these kinds of ebbs and flows. But when the summer clothes came out, an old thought pattern was triggered. Suddenly you were critiquing your body again, obsessing over how a top fell or a dress pulled. Maybe this felt like a failure twice over—a failure to live up to some invisible beauty standard, a failure to not care about that. To buy new clothes, then, would be to cave to the same value system you’d been trying to dismantle.

There’s another interpretation though. I’d argue that your penchant for denying yourself pleasure lives on in your relationship with consumption. I don’t mean to say your efforts to consume less—to save money, to vote with your dollar, to be environmentally responsible—aren’t admirable. If these values are important to you (as they really should be to all of us), I agree you ought to find ways to foster them. But I don’t think you should set a trap whereby you’re only a good and worthy person if you behave perfectly in accordance with them, even when you have genuine needs to the contrary. Considering your history with food and exercise, maybe that trap sounds familiar.

You can buy things for yourself sometimes. Do things just for pleasure sometimes. Be moderate, then not be moderate, and allow things to steady themselves out. Just because other people abuse these notions to be flagrant doesn’t mean they’re universally wrong. They contain important truths about the human condition—about giving ourselves over to the experience of life and surrendering to what we can’t control, like our hunger for food and for love. Control is a fool’s errand. “Self-improvement can be self-sabotage,” Adam Phillips once wrote. “Too knowing; too knowing of the future.”

If you want to unravel the punitive element of your disordered life, the answer is not to simply direct your desire for perfect thoughts and perfect behaviors at a new goal. You don’t want to replace one punishment with another. The goal, I think, and I say this to myself a lot too, is to find motives other than getting straight As. Presence, pleasure, connection, curiosity, tenderness, variety, surprise, care, love. There are so many ways to be attentive to this world (and respectful of it) that don’t concern self-discipline.

To some, this may sound like a justification for hedonism, especially since I’m saying it in response to your very reasonable desire to watch your spending. But I think that’s a misreading. Your desire to consume thoughtfully is commendable and worth respecting, but I’d still urge you to go easier on yourself. It’s okay to take pride in your presentation; to buy things from time to time for logic or pleasure’s sake. It’s not one-negative-thought-in-the-mirror-and-now-you’re-back-in-the-deep-end-obsessing-over-everything-and-caring-about-all-the-wrong-things (note my excessive use of hyphens, felt good). You can have a little vanity, as a treat. It’s also part of life.

Everyone has a point at which their desire for new clothes surpasses the reasonable (or even the pleasurable) and becomes destructive (to the self, to the Earth). That point may be different for different people, and it’s great that you’re cautious of where that point is for yourself, but I think your calculations are a little off, still influenced by the self-policing impulse that first ignited your disordered behavior. Consider this change in your body an important challenge not just in accepting change, but also in recognizing change may invite a little grief, and even require a little tending, in different forms, of course, and within reason.

On “financial incompatibility”

“Dear Baby,

I’m turning 30 this year and I am happy in my relationship much of the time. We often speak of a future together. But I’m scared we may not be financially compatible and I don’t know what to do with that fear.

I recently saw Materialists (not an ad, I swear), and while I liked parts of it, it left me frustrated. Its takeaway seemed to be: love conquers all, even money. But money isn’t just a hurdle. It’s a force. It complicates and corrodes. It shapes everything. And I’m starting to worry the future I imagined for myself is slipping away the longer I stay in this relationship.

My partner is warm, creative, emotionally present. He says he wants the same things I do—stability, a family, a shared life—but his follow-through is inconsistent. He moves between passions quickly. He resists structure. I don’t see a clear path forward, at least not one we’re building together. I want to be able to suggest a restaurant without obsessively checking the menu prices first. I want healthcare and housing. I want to go on trips with our friends. I want children someday, and a partner I trust to share the weight of that.

I want to talk to him about getting on the same page and about what it would take, realistically, to build a life together. I want to ask him to pursue something more stable if we’re serious about having a future. But I don’t know if I can ask that of someone. Or if I should. Maybe the fact that I’m even asking these questions is a sign that we’re not right for each other. Maybe we’re just two people who love each other but want different things. A tale as old as time!

I don’t want to ignore the fact that my long-term goals matter and that I need a partner I can realistically get there with. How do you love someone and still ask them to change? And how do you know if what you’re asking for is fair? Or if you’re just asking them to become someone they’re not?”