A coworker has asked me for money several times and never paid me back. Now he's asking again. I don't want to hurt his feelings, but I'm fed up with it. How do I turn him down without damaging our relationship?
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.
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.
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