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One of the best adjustments I've made in life is no longer loaning money to people. I used to do it a TON in my youth, and it was really sad how often people ended up resenting me over their guilt about owing me money. What I do now instead is just give people money. No expectations, no conditions.
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Obviously I don't hand it out like candy (would that I could), but by just giving the money away I avoid that weird guilt situation for the most part and people are more thoughtful about asking me for help because the dynamics are different.
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What I usually ask people to do in lieu of paying me back is to help someone else when they have the opportunity.
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They won't. But you have still won control over the situation because you have taken charge of how you deal with this.♥️. Maybe in future you'll make another change.