I have been pressuring a friend who is not doing well to give

>>17521117
How much dough is it?

Hire some guys to rough him up a little.

>>17521119

$200

He has written me a check and I can fuck him up with it...

...but, I really think I should let it go.

>>17521117
loaning people money like never goes well,
it just makes socializing super awkward even if it was well intentioned.

You can phrase it in terms of there's no time prerogative and that it's just a drop in the bucket for you. He'll probably still feel guilty about it indefinitely and it will probably hurt your friendship.

>>17521124
The best way to do it, assume you truly just want to avoid hurting his feelings and finical situation, is to not cash the cheque and just not bring it up anymore. At worst, he'll eventually ask why you didn't cash it, and you can either be like "I did" or "oh I'll get to it" but I doubt he'll ask.

>>17521117
>What's a good way to say that without appearing as if I am doing this for charity / pity?

I am interpreting this to mean that the money is not a big deal. But, you dont want to set the precedent for your friend thinking they can borrow money without returning it, whether it be you or anyone.


Given that assumption simply tell him how you feel: Hey, I just wanted you to know that i have been expecting the money you borrowed for quite some time. I know that it may be impossible for you to do so currently. If you had asked for money outright, i probably would have given it to you. But it is frustrating that i gave you money with the expectation of being paid back and i havent heard anything from you whether it be why you cant pay or when you will be able to. I have tried to communicate with you, but you close up due to the sensitivity of the subject. I do not expect the money back, but it does not change the fact i felt i have been lied to. I hope we can redevelop trust in one another in the future.]

TLDR lay that guilt trip on thick.