Woe Is Me! is a series in which The Swaddle team indulges your pity party with advice you’ll probably ignore.

“I recently walked in on a friend taking out money from my purse. She returned the money and said she was going through it because my phone was ringing. It obviously felt like an excuse — if what she said was truly the case, she would have picked up the phone, not the money. I didn’t say anything about it then — I thought I should just let it go, but try to be more cautious around her. However, yesterday, I accidentally left my purse alone around her again and I feel like I have lost money (around Rs. 300). I don’t always count my money, so I am not sure –maybe, I am overthinking even. The things is, we have been friends for over two years, and until now, I thought we were really good friends. But I don’t know anymore. It’s not like she is going through any financial crisis; she comes from a pretty well-off family and even if she was having money problems, stealing is not a solution. What should I do? I keep thinking that I shouldn’t end a friendship over money; she is, after all, the only friend I used to hang out with every day in college. Should I confront her about this? Should I just pretend that nothing happened, and just be more careful of her in the future? Or should I just distance myself from her?“

— Honey, honey, don’t take my money

AS: Well, I agree with you about one thing — that one shouldn’t end a friendship over money, be it about someone’s wealth, or lack thereof. But this isn’t about money, is it? It is about dishonesty and going behind a friend’s back. If it weren’t a close friend, I would have advised you to let it go, or be more careful going forward, especially if you’re a non-confrontational person, like I am. However, since this is someone you’re close to, it is important to talk to them. If you don’t want to confront them now or you’re not sure, you could wait, and do it if something like this happens again. But sooner or later, you’re going to have to bring it up. It’d be best to make sure you’re empathetic — maybe they’re going through something at home? Or could it be compulsive? Do your best to give them the benefit of doubt, and help them get the assistance they need. If they don’t come clean, or if there’s something seriously amiss, you should consider parting ways — because what is friendship about, if not trust and honesty?

RN: Here is an unpopular opinion: if the small sums of money aren’t hurting you, let it be. I always tend to give people who do this the benefit of doubt: what would compel them to risk their relationships, public standing, and reputation like this? The circumstances have to be dire, whatever they are — or she could be experiencing kleptomania. In any case, if she’s been your friend for a long time, I think you should be concerned rather than affronted. The fact that you’re considering cutting her off without asking or enquiring after her situation makes you out to be a little unfeeling in this scenario. What if she has no financial agency in her family? What if she’s cut off from her family’s finances for her own personal use? What if she needs the money for something her family doesn’t approve of, like perhaps a medical procedure or some kind of application? I think you can gently ask her if she’s going through financial issues if you’re going to bring this up at all, but by no means cut her off entirely for something like this. Having said that, I do acknowledge that she should also be considerate of your financial situation and think about whether you may need the money for similarly urgent reasons. It’s worth a conversation to find out more, but my hot take is that stealing is a completely misrepresented crime with way too much of a moral panic attached — context and power dynamics always matter when thinking about this.

SK: As implausible as this might sound, I had a very similar experience with a friend some years back. After a series of very suspect and inexplicable events, I carried a sneaking suspicion that my friend had stolen money, and an artifact from my home. I never brought it up with her and tried to move past it, but it did change how I engaged with that friendship and eventually ended up distancing myself from her. I’m unsure if I handled it correctly; the moral absolutes of rightness and wrongness don’t seem adequate to gauge the situation here. But I do look at the situation differently today. So when I say I understand the loss of trust and uncertainty you feel, I truly do. It feels like erosion of principles, of an understanding two people reach in a friendship.

I will agree this is a really awkward situation. But at the same time, there has to be room for belief in spite of doubt. If it’s bothering you so much, you should probably subtly bring up the fact that some money is missing. Then maybe you can ask her if all is well with her. Once that is done, you can gently tell her that it’s bothering you a lot. Gauge her reaction, if she still doesn’t respond then confront her. It’s better to get it out of your system, otherwise, it will only color your relationship.

DR: I know you’re in a tricky situation that’s, perhaps, also unprecedented for you. So, while I don’t blame you for freaking out, I’ll say this: if you’ve already branded your friend a “thief,” instead of branding just her actions as “stealing” — that too, possibly, and not as an established fact — what, really, is left to salvage of your friendship with her? Friendship, just like any other relationship, involves a degree of mutual respect and trust, which seems to be lost here — at least, from your end.

Having said that, I don’t think you’re wrong to want to be on guard — I’ve no idea what your financial situation is, so I think it’d be mighty privileged of me to decide whether you should be outraged, and if so, how much. Just to add perspective, though, is it possible you might be unaware that she’s facing some sort of financial crisis? Some people manage to do a good job of preventing others from catching a whiff of it by keeping up appearances — speaking from personal experience here. Or, she could be struggling with kleptomania, and may or may not have even come to terms with it — let alone figuring out a strategy to stop acting upon it. I’m not trying to necessarily absolve her; just telling you there could be more to this even if she’s indeed stealing from you.

I would’ve suggested sitting down with her for a calm, polite conversation on the subject. But given that I don’t know whether she’d be able to navigate this with honesty, or even emotional maturity, I don’t want to advise it as the way to go; instead, I want to tell you that it’s one way to go, should you, based on your understanding of who she is, think it won’t end badly.

If not, I’d suggest you minimize how much time you spend together for a little while — to give yourself the space to process how you feel about this and whether you’ll be able to move past it and trust her again. If not, it’s okay to let friendships go too. If you do want to go ahead and salvage it instead, I think it’s important you try to find out ways she can regain your trust — possibly, by letting her know of the things that have been bothering you — so you don’t have to be on tiptoes around her anymore. That will, hopefully, give her a chance to explain herself too — besides sharing your burden of building back the friendship.