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How to lend to someone who's struggling without making it weird
My friend Rosa told me she’d lost her job while we were standing in line for tacos, and she said it so casually that I almost missed it. “Oh, yeah, they let me go last week. Anyway, are you getting the al pastor?”
I knew Rosa well enough to know the casualness was armor. She’s the person in our group who organizes everyone’s birthdays and always has a spare phone charger in her bag. She’s not used to being the one who needs something. And I could tell, even then, that asking for help was going to be about the hardest thing she could imagine doing.
A couple of weeks later she did ask. She needed $800 to cover rent and her car insurance while she figured out her next move. I said yes. Then I spent a fair amount of time thinking about how to make the whole thing feel less awful for her, because I think the way you lend to someone who’s struggling matters almost as much as the lending.
Make yes the easy part
When someone works up the nerve to ask, they’ve usually rehearsed it. They’ve probably also rehearsed you saying no, or worse, you hesitating and asking a bunch of questions about where their money went.
So if you’re going to say yes, I think it helps to say it quickly and plainly. Not “Hmm, let me think about it” followed by a three-day wait, and definitely not “Well, how did this happen?” Just “Yeah, of course. Venmo okay?” The faster and lighter the yes, the less time they spend feeling like they’re on trial.
If you need to say no, or you can only do part of it, that’s okay too. Say that plainly as well. A kind, quick “I can’t do $800 right now, but I could do $300” is so much better than a vague maybe that leaves them hanging.
Keep it between the two of you
This one should go without saying, but I’ll say it anyway. Don’t tell people.
Not your other friends, and not even in the “I’m just worried about her” way. I know the impulse comes from a good place sometimes. But news like this travels, and the person who’s struggling will almost always find out, and then they’re dealing with the money stress plus the humiliation of everyone knowing.
It also means not acting differently in public. Rosa still picked up the check for my birthday drinks a couple of months later, which made me wince a little. I wanted to stop her. I didn’t. Stopping her would’ve been a way of announcing, in front of everyone, that I knew she was broke. Letting her be generous was part of letting her keep her dignity.
Let repayment bend
This is where I think a lot of friend loans go sideways. Someone lends money with a vague idea of when it’ll come back, the person who borrowed can’t meet it, and then nobody talks about it. The silence turns into avoidance, and avoidance turns into distance.
With Rosa, I said something like, “Pay me back whenever you’re back on your feet. No rush, and if you want to do it in pieces, that’s totally fine.” I meant it. And I think saying it out loud took a lot of pressure off. She didn’t have to wonder if I was quietly counting the days.
Flexible doesn’t mean you never bring it up, though. Months later, after she’d started a new job, I checked in once. Not about the money exactly. More like, “How’s the new place? You settling in okay?” She brought up the loan herself in that conversation and said she wanted to start paying me $100 a month. Perfect.
If you do eventually need to nudge, I think a short, warm message works best. Something like:
Hey! No pressure at all, just wanted to check in on the $800 from the spring. Happy to keep doing it in chunks whenever works for you.
Specific about the amount and gentle on timing. I’d send something like that once and then mostly let it be.
What I keep circling back to is that the person who’s struggling is already doing a lot of internal math. They’re thinking about what you think of them. They’re wondering whether this changes the friendship. A lot of what you can do is quietly answer those questions with how you act, so they never have to ask them out loud.
Rosa paid off the last $100 in November. She sent it with a photo of the same taco truck and a caption that said, “Lunch is on me next time. For real this time.”
It was, too. She even got me the extra guac.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.