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How different generations think about lending money
At my cousin’s graduation party last summer, my dad watched my teenage cousin Hailey send her friend a Venmo request for $4.50 for a lemonade, and his face did something I’ve only ever seen it do at the gas pump.
“Four fifty?” he said to me, quietly. “She’s billing her friend for a lemonade?”
To him, this was borderline offensive. To Hailey, it was completely normal, about as emotionally charged as liking a photo. And to me, somewhere in between, it was a perfect little snapshot of how differently the people in my family think about owing each other money.
I’ve been chewing on it ever since.
My grandmother’s generation, at least in my family, did nearly everything in cash and kept nearly all of it private. I wrote a while back about her green notebook, the one where she logged every loan. What I didn’t mention is how quiet the whole thing was. Money was handed over folded, often in an envelope, often in the kitchen when nobody else was around. Nobody talked about it at the dinner table. There was a pride thing tangled up in there too. Asking for money was a big deal, almost shameful, so the lender’s job was to make it as painless as possible. You didn’t make someone feel small for needing help. You helped quietly and wrote it down, and nobody else ever heard about it.
Favors worked the same way, with a twist. Sometimes nobody wanted money back at all. Instead there was this vast invisible economy of casseroles and rides to the airport, all of it understood and remembered, none of it written down. You didn’t pay back a favor with cash. That would have been almost rude. You paid it back with another favor, maybe years later.
My parents came of age with a slightly different attitude, I think. They kept the pride but dropped some of the softness. My dad, in particular, has always treated borrowing as something close to a moral failure, at least for himself. He’d rather eat ramen for a month than ask a friend for $200. When he does lend money, it’s with an unspoken but very clear expectation that it’ll come back, and if it doesn’t, he doesn’t argue. He just quietly stops lending to that person forever. My mom calls it “the list.” Nobody knows who’s on it, but everybody suspects.
Checks were a big part of their world, too. My parents still occasionally write checks to friends to cover things, which feels a little like watching someone send a telegram. There’s a certain formality to it that I sort of admire. A check has your signature on it. It’s a little document. It says, “This is real.”
My mom, to her credit, has made the jump to Zelle. She uses it the way she used to use checks, though, which is to say slowly and with great ceremony. She’ll call to tell me she’s sending money, then send it, then text to confirm it arrived, then call again if I haven’t replied to the text. The app is new. The instinct underneath it isn’t. For her, money between people still deserves a little paperwork, even if the paperwork now lives on a phone.
Then there’s my generation, the people I actually hang out with, somewhere in our thirties. I think we’re kind of the hinge. We remember cash and envelopes, but we live on Venmo and Zelle. We split things more evenly than our parents did, maybe because so many of us went through lean years in our twenties and got used to dividing every pizza six ways. We’re more likely to talk about money openly. But we’re also, honestly, more prone to the slow drift. A few $15 Venmos that never quite get sent. A rotating “I’ll get you next time” that quietly stops rotating.
And then there’s Hailey’s generation. They’re the ones who would genuinely send a $4.50 request for lemonade without a second thought, and what took me a while to realize is that it’s not because they’re stingy. It’s almost the opposite. For them, a request isn’t an accusation. It’s just bookkeeping, done in two seconds, with an emoji attached. There’s no shame in it and no pride either. Hailey once explained it to me like this: if she requests it right away, it’s over, and neither of them has to think about it again. No lingering awkwardness three weeks later. Her friend pays, and they move on.
I’ll admit that kind of blew my mind. My dad sees the request as cold. Hailey sees it as the thing that keeps it from getting weird. They’re both trying to protect the friendship, just from opposite directions.
I don’t think any generation has it figured out completely. My grandmother’s quiet, generous lending made people feel cared for, but it also meant some loans just evaporated because nobody wanted to bring them up. My dad’s list protects him, but it’s probably cost him a friendship or two he didn’t need to lose. My friends are more open and also more scattered. Hailey’s crowd might be the most efficient of all, though I do wonder whether something gets lost when every lemonade goes on the books.
If I could mix and match, I’d probably take my grandmother’s notebook and Hailey’s speed, and leave the list where it is.
Later at that party, I saw my dad buy Hailey a lemonade. She tried to send him $4.50. He declined it, and she stared at her phone like it had personally betrayed her.
The OweMate blog is written by the people who make OweMate, a simple way to keep track of money between friends and family.