https://www.800loanmart.com/getting-and-using-a-loan/how-to-ask-a-friend-to-pay-you-back/
Be Direct When You Ask To Be Paid Back
Asking someone to pay you back is not fun, but sometimes being direct and asking face-to-face is necessary. “If you’ve seen no movement on their part to pay you back, just ask,” Grace says. “Say, ‘When do you think I can expect to see a payment?’ or ‘Hey, can you electronically send me the money I lent you?’ or ‘Can we set some repayment schedule for the money you owe me?’”
While it can be uncomfortable to reach out to someone and let them know you’re still waiting to get paid back, there are ways to make the conversation free of tension for both parties. And often times, the person you loaned money to just forgot. “Don’t assume the person is ignoring you,” Woroch says. “People get busy, and if someone forgets to pay you back, don’t be on the attack right away. Give them a chance and call to politely ask for that money to be paid back.”
TL:DR? Before loaning a friend money, make sure you’re comfortable with asking for it back — and OK with potentially not getting it back.
Drop hints about needing money
No one likes asking for money, and it's safe to say that no one likes being asked for it either. Although you might not see it this way, it's equally stressful for both parties, so the less painful you can make it, the better.
Rather than coming straight out with the "give me my money back" bombshell, try dropping a few hints here and there first – something like, "Sorry, I can't come to the pub tonight, I'm too skint."
If your friend is sharp enough, they should be able to pick up your hints and you can avoid having that dreaded conversation altogether. Worth a try!
Highlight your own financial situation
This is similar to the above point in that you can make your friend more aware of your own situation and encourage them to be a bit more empathetic.
Add a sense of urgency
Adding a sense of urgency to your request will help your friend to understand that you are now in a tricky financial situation after lending them the cash.
Phrases like, "I'm sorry to ask this, but I really need that money to pay an energy bill by the end of this month", would work well. Don't set the deadline too soon, though, otherwise you could get your friend into a real panic.
Give them a bit of notice so they can scrape the cash together first.
Be flexible about receiving money back
Depending on the circumstances of your situation, like how much money it was that your friend originally borrowed from you, it might make the situation a bit less stressful if you suggest they repay you in a few instalments.
This way, you can start seeing at least some of your cash again, and it will show your friend that you really are sympathetic towards their situation.
Find a way for them to work it off
If money is an issue for them, then maybe you can find some kind of favour they can do to wipe the slate clean. If they're a designer and you need a logo, can they do that for you and call it even? If they fix cars, could they take a look at yours and give an honest opinion about work that needs to be done? Everyone has some kind of talent or skill they can provide, and if you need it, they may appreciate the offer.
Barter for something they have that you want
This is another good way to get money back without actually having your friend pony up the cold hard cash. Is there something that your friend has that you would like? It should be of equivalent value to the cash you loaned them, so keep that in mind. Don't go asking for a flat screen TV because you loaned them $20. But if you know of something, and you think they'd be more than willing to part with it, give it a try. Maybe they have two of something, and would be happy to give you one. That would be an ideal way to make everyone happy.
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