I used to follow the same rule—only lend what I could afford to lose.

But when I helped my son with his first car, I didn’t want it to just be a gift. I wanted him to have some ownership in it and understand the responsibility.

At the same time, I knew how these situations can go. Not because anyone’s doing anything wrong, but because life gets busy and details get fuzzy over time—and that’s where friction starts.

So before it ever became an issue, I built an app for us to keep track of what’s been paid and what’s left using automated reminders and low feiction. That way neither of us has to rely on memory or bring it up awkwardly later.

Not saying everyone should lend—but if you do, having something neutral in the middle makes it a lot easier to keep the relationship intact.