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There is nothing worse than having to ask a friend to return the money they borrowed from you, apart from the fact that it can soil the friendship, you may also lose the money. It’s pretty tough. Asking for money from friends can feel really awkward.
Debt ruins relationships. I never loan money to friends unless I am willing to lose it or forget it, they may get weird about the debt and not want to look me in the eye. I suggest having him pay for lunch every time you go out and get the money back little by little. You also want to use the opportunity to get other favors out of him that can help pay down the debt.
For your sanity I think you need to forget the debt in your mind. It’s just money and people are more important than money. It would be nice if your friend thought the same way and just paid you back. It might be wise to forgive him the debt and then not be his friend anymore.
I really don’t think you will get your money back, but if you have some documentation you can try. You might need to accept that your money has gone, and so the friend is also better off out of your life. The only other thing you can do is learn from this experience, don’t lend money unless you can afford to give it away. In other words, if you are going to stress about when you will get the money back, don’t offer to lend it in the first place. If you can afford to forget that you gave someone money, you will be pleasantly surprised when they pay it back. Don’t undermine your own financial security to do someone else a favor when they have no intention of helping you out in the same way.
If someone asks to borrow a certain amount of money, you are not obligated to lend it even if you are in a stronger financial position. You can simply say “I can’t afford to lend that right now.” Even if you have the money in your hand, doesn’t mean you can afford to lend it.