Money vs. Friendship

I lent out a small amount of cash—nothing crazy by objective standards, but given my salary, it actually matters. Especially since I know exactly how much they worked me to death at my job just to earn it. The deal was simple: a friend would pay me back once he got his paycheck. One month passes. Two months pass. Nothing. I didn't say a word—figured he’d bring it up himself—but then he goes and quits his job. At some party, he finally mentions he'll pay me back and that he’s feeling awkward about it. I played it cool; told him it wasn't urgent and to just pay whenever he could. Fast forward to today: I hear from another friend that this guy is out every weekend, spending money, living his life. Now I’m the idiot 🤷 It’s been roughly nine months now 🤷 though does it even matter?

If I just write the money off in the name of "friendship," I end up kicking myself for being naive enough to lend money to friends—or for being too hesitant to demand it back. My gut tells me to go after it, yet part of me just wants to say, "forget the cash, I won't starve without it," and vow never to lend a dime to anyone again.

Those kinds of situations usually involve friends and money. I guess you might be worried that asking for your money back will make you look like some kind of cheapskate, especially if it’s not a huge amount, but my advice would be to never let anyone take advantage of you when it comes to what's yours. You should just ask for your cash back and try not to worry too much about what people might think or say.

I’m feeling the exact same way—working my ass off for maybe three grand a month, and even then, after all the excuses they pull, I usually end up with less. Looking at it now, I realize this is barely 1/6th of my pathetic paycheck.

Flip the script for a second. Imagine you’re the one who lent the cash. If you weren't planning on paying it back—which, let's be real, doesn't sound like your style—you'd just write it off. But if you actually intended to pay? You'd want your money back. Forget being polite or feeling awkward. These are your funds that you earned with your own hands. You lent them; you didn't gift them. Sure, the fact that he’s unemployed right now makes things messy, so maybe meet him halfway by giving him a month or two—whatever timeframe he needs to scrape that amount together. Just stay firm. Don't feel guilty or embarrassed about asking for what's yours. Honestly, he should be the one feeling the shame for failing to pull this together after nine whole months. I bet he'll try to play the "I don't have a job" card, but I’d just "gently" remind him he had a steady paycheck when he took the loan in the first place. That usually shuts down those kinds of excuses pretty quick. Just heads up: don't be shocked if he starts acting like a total diva and tries to make you look like the bad guy for squeezing a "poor, jobless guy." People love to conveniently forget the most important part of the equation in situations like this. You lent him the money because he asked for it. You didn't force him to take 🙂

Oh, and if I were you, I wouldn't bring up stuff like "well, you clearly have money for drinks and cigarettes." That's just asking for a massive blowout.

Demand your money back; if they’re a true friend, they’ll understand. You could always suggest a payment plan if they can't settle the full amount right away.

I didn't actually intend to bring up his spending on nights out or cigarettes—that’s his business—it just looks a bit questionable from my perspective. 🤷 Everyone operates differently, I suppose. But if I ask for my money back and mention I need it soon, it isn't even a lie; I have plenty of plans lined up that require a larger budget.

Honestly, I’d just give him a call and let him know I expect those funds to be added tomorrow. I wouldn't make a scene about it; I’d just ask what time he plans on swinging by. No hostility, no drama, no attitude—just keeping it strictly business. Everything is fine, but we are definitely settling this tomorrow.

He called—said he'd let me know when he needed me, promised it wouldn't be an issue. So maybe I was just being dramatic for nothing 🤷 considering how much of a mess things are with that money

Are we talking about a ride-or-die best friend here, or just some random acquaintance you run into at the coffee shop?

Nothing's a done deal until you actually see the cash in your account. Besides, you even mentioned up above that he already promised to pay you back 🤷

Brandon Lopez6 said:Nothing's a done deal until you actually see the cash in your account. Besides, you even mentioned up above that he already promised to pay you back 🤷

That's true enough. But that was more of a "yeah, I'll get you back" without any actual timeline attached—and I even told him to just pay me when he had it, since I didn't really need the money at the time. We've settled on a rough timeframe now, so we'll see how it plays out. If I ever bring this up again down the road, you'll know the money hasn't surfaced.

Look, I’m rooting for you either way—really hope you get your money back. Honestly, though, I think bringing up interest rates right now might be a bit much. 😬

Brandon Lopez6 said:Look, I’m rooting for you either way—really hope you get your money back. Honestly, though, I think bringing up interest rates right now might be a bit much. 😬

I think I will, thanks.🙂

If they actually offered it to me, I’d pass—I’m not exactly looking to play philanthropist😁 but honestly, nowadays even the people borrowing the money don't seem to care. They act like if I happen to be lucky enough to have some cash sitting around, it's my responsibility to fund them.🤷

At least you can put that beer on a credit card😁

People are unpredictable, I guess. Not trying to make excuses for my buddy here, but he lent money back when things were solid. He had a steady gig and probably thought, "No biggie, I'll have this back to you in a month," only to have that happen a few times before he lost his job. Now? He might actually be struggling to scrape it together. Still, that’s his mess to clean up, not yours.

Lesson learned: don't go handing out cash so easily in the future. So many friendships have gone down the drain because of this exact thing. Like you said, people just assume you'll bail them out because that's what you do. But honestly, making $2,500 isn't some charity fund meant for everyone else. You didn't get that paycheck as a gift to hand out to whoever asks—what you do with your own money is your business. 🙂

The train fare was easy—neither he nor I would have had any trouble covering that.

It’s not that I’m judging him, per se; it just feels off. Looking at it from my side of things, if he actually felt an obligation to pay me back, he’d have done it the second he had the cash. Someone always ends up losing out in these scenarios, but a debt is a debt. If I didn't need the money by a specific deadline, I probably wouldn't even be bringing this up.

I don't lend money anymore. If anyone asks, I tell them I don't have any—which, frankly, will likely become a reality pretty soon. End of story.

The biggest screw-up we all make is thinking everything revolves around our own point of view. At least, that’s how it’s always played out for me. People usually end up doing the exact opposite of what you had in your head.

Mistakes are just lessons in disguise.

Andrew Mendoza10 said:Mistakes are just lessons in disguise.

What kind of figure are we talking about here?

Douglas Gray8 said:What kind of figure are we talking about here?

He mentioned lending out a sixth of his paycheck, which was about 3 grand, so basically $167 🙂

Brandon Lopez6 said:He mentioned lending out a sixth of his paycheck, which was about 3 grand, so basically $167 🙂

Not exactly a fortune. Barely covers three of my daily shifts.🙄