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Has he ever paid you back any of that money at least?

If he didn't pay anything back, then it's not a debt anymore, it's a gift you gave against your will. And to the next request you can just answer: "Can't help, I'm tight on finances right now". There's no lie here - if you've already lost money on one person, then you really are tight on finances. No need to explain, apologize, or talk about your budget. Just a calm refusal, no extra words.

If things are already awkward between you, you can add a bit of softness to your tone, but don't change what you're saying. Like: "Look, I've helped you more than once already, and the money never came back. So I can't lend money anymore, nothing personal". The guy will either get it or get upset, but that's his choice. But giving money to someone who won't pay you back - that's your choice, and you'd better change it right now. After you refuse once, chances are there won't be a second request.

Maybe he's just not counting on returning it and betting on you being too embarrassed to ask?

If after a few requests nothing's been returned - it stopped being a debt a long time ago. You basically already gave him that money, just in the form of a "loan." If you keep repeating this scenario, you're only hurting yourself and reinforcing his belief that it works.

For the next request, you can answer without a lot of explanations: "No, I don't do this anymore. You didn't return the previous debts, so I can't help you." No apologies, no excuses like "I can't right now." It's more honest than lying about not having the money, and it shows you're serious. Most people just stop asking after that.

Life hack: if you're afraid of a direct refusal and know you'll end up justifying yourself - write to him in a message. It's easier to stick to your position in a chat or email and not give in to complaints or persuasion. When you hear someone's voice or see their face, it's harder not to break. Writing is your safety net.

Максим asker Yeah, he clearly thinks that's a safe way to do it. Thanks for the tip about putting the refusal in writing - that'll definitely help me not cave to complaints.

The thing is, what will damage your relationship here isn't your refusal - it's his requests. You've already said "yes" several times, and nothing has changed. That means trying to be polite and considerate isn't working anymore. He's gotten used to you giving him money, and he'll keep asking because it works for him.

I had a similar situation - an acquaintance would borrow from me right in the work cafeteria between lunch breaks. I'd give her money, she wouldn't pay it back, then she'd ask again. I was embarrassed for a long time to just say "no" outright, afraid of damaging our relationship. In the end, when I finally refused, it turned out she wasn't even offended - she just moved on to the next person. Later I realized she never actually expected to pay the money back at all; she was just testing who would give it to her.

Next time he asks, just say: "Unfortunately, I haven't gotten back the previous amounts I lent you, so I'm not able to give you more." Don't apologize, don't explain how you budget your money. It's direct, calm, and fair. If the person is actually reasonable, they'll understand. If they get offended - well, that means the relationship was built on the idea that they could count on you for money, and that's not your fault.

The easiest thing to say is: "I'm in a tight spot with money right now, I can't help." It's a universal and honest answer that doesn't require explanations and doesn't sound like a personal rejection of him specifically. If he keeps pushing, you can add that you have a rule - you don't lend money to coworkers at all, it's simpler than bringing up past debts. The main thing is to respond calmly and confidently, without apologies or justifications, because honestly you don't owe him anything.

I've been in that situation too and struggled with it for a long time 😅 The thing is, it's not really about how to politely refuse - it's that politeness won't help if someone's already borrowed multiple times and never paid back. That means they either can't or won't, and they'll just keep pushing if you give them a polite no.

I ended up just telling them straight: "I'm not going to lend money anymore because it ruins my mood" - blunt and straightforward. We stayed on good terms, but the requests stopped because they realized I was serious about it.

The key thing here is understanding that politeness isn't a free license to use you. If someone has already not returned money several times, they either can't or won't. Either way, that's their problem, not yours.

Just say: "I can't do it this time, and I'm not promising money anytime soon." Keep it short, no details and no excuses - the more explanations you give, the more reasons they'll have to negotiate. If they start pressuring you or getting offended, calmly say: "It's my choice, and I'm not going to change it." In this case, damaging the relationship won't be because of your refusal, but because they don't want to respect your boundaries.

If things get colder between you after that - well, that's a sign the relationship was built on what they could get from you, not on normal interaction. You won't get anything out of dealing with someone like that anyway.

The main thing is don't pretend you don't have money if he knows you do, or will find out eventually. It's better to just be honest and say: "I don't lend money to people anymore, because it ruins relationships" - it sounds firm but not aggressive. If he insists, you can add that previous loans were never paid back, so you decided to stop. It's not about being hurt, it's a sensible decision, and a normal person will understand that.

If he hasn't paid back anything after a few times, then you can just stay silent - it's more powerful than any words. When he asks next time, pause for a second or two, and he'll get the message that the answer is no. His audacity is what'll damage the relationship here, not your silence.

Or just tell him straight up: "I'm not getting back the money I lent you before, but I can't help you anymore." It's blunt, but fair and honest.

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