To ask friend how she will repay

I agree if its as simple as this and not the friend having intentionally used op.

Please dont be apologetic when you get in touch again. She wants you to feel guilty.

She is a cheeky cow! She never intended to pay you back

"come out of the woodwork" 🙄 What an unpleasant and inaccurate phrase.

The OP might need that money now and even if it's just to bring her back to where she was before she loaned the money it's still OK to establish that that's going to happen in an acceptable time frame which is all the OP was asking. To imply that she's somehow being mean for doing that is totally, totally unfair.

I agree with others in that you either write it off, if it's a small enough amount or you come back to her with a payment plan. Ignore all the emotional blackmail completely. Message something like, "Thinking about the loan going forward, I suggest X amount every month. Here are my bank details." If she comes back with more about being shocked and upset just be cool with her. "I appreciate it's difficult for you but unfortunately I'm not in a financial position to gift anyone large sums of money and would appreciate setting up the repayments ASAP."

I have a couple of rules I've never broken in 50+ years. Never lend money to friends. Never rent my properties to friends. It clouds judgement over where the line is drawn . . .

She's not paying you back. Trying to shut you down when you asked for some of your money back makes that clear. You might have to write the cash off and cut her loose as a 'friend.'

I'm sorry to say that you've been had @BigMommasHouse
You need some leverage. Can you trick her into lending you something reasonably valuable and then hold on to it for security until you get back what you've loaned her.

'I haven't demanded the money back'
I know you see this as you being kind and reasonable but she looks at you and she sees a soft touch. She knows that she can ignore you and fob you off and there's nothing you will do about it.
She's clearly a chaotic person who isn't capable of managing money... and you thought she'd come up with a plan for paying you back?
Come on, wise up girl!

"I realise that lending money is a mine field but I genuinely thought I was doing a good thing for a friend who was at rock bottom."

I think this is the line you go back to her with, in person or by text if she's now avoiding you.

It's great that she's becoming solvent again but debts need to be settled. That's not greedy or inappropriate, that's just fair.

And if you get the "is this amount worth losing our friendship over...." tell her she's creating that situation not you. You only did a good thing, I'm sorry it's panned out like this.

Most employers will say no, out with special circumstances like starting and needing money before pay day, if you've just started.

This is exactly what happened to me with a friend. I lent her money because her business collapsed. The next thing I know, she's off on a luxury holiday.
I did get the money back, but it took some 4 years. No interest. Destroyed our friendship. Will never lend money again.

This post is confusing: “I’ve lent money to friends but never expected it back”. Then it was a gift, not a loan and you could afford that.

Then ”If I’d given money to friends… I’d never come out of the woodwork demanding it back as soon as they got both feet back on stable ground”. If you’ve given them money then you’ve no business ever demanding it back. It’s a gift: it’s theirs.

I think you need to accept that you have probably lost the money, the friendship, or both.

Someone who organised a holiday while owing me money wouldn't be a friend for long.

I think you have to be prepared to not see any of that money again. Do you have evidence it was a loan, messages etc?

I would be prepared for the friendship to be over if she tries to carry on with the emotional manipulation.

I'd say to her that of course you don't want to fall out either which is why you've put off mentioning it while she was getting back on her feet. But now she seems to be doing better you thought it was best to discuss it, since you've always had an open and honest relationship. And reiterate that you haven't asked for it all back immediately but would like to understand what the plan is so that you can plan your own finances, which you don't think is unreasonable.

She’s not going to pay you.
And you’re the bad person for reminding her of the debt.

I have lent money to a family member. I wrote down the loan and payment plan and we both signed it.
My reasoning is if you went to a bank you would have to sign for a loan.

Having a proper plan written down makes the borrower more likely to honour the
agreement.

Do you have a list of dates & amounts?

I would present this to her and say something along the lines of I've lent you X over X period and I have always been happy to help out when you really needed, however, I thought we both knew it was a loan and not a gift. I am unfortunately not in the position to gift you this amount, and do require paying back, however, I am happy to come up with a payment plan so it's not a big hit in one.

...and never lend her money again. Also, be prepared to not get your money back and loose a friend if she refuses.

She's manipulating you. She shouldn't be shocked that you've asked about the money she knows she owes you. She shouldn't be threatening your friendship with it.

@BigMommasHouse As others have asked, did you make it absolutely clear when you loaned her the money ( every time) that you did expect it to be repaid when she was on her feet again, or did you just assume that it would be repaid?

If the former, then she is a CF. If the latter, then she probably thought it was a gift and as others have said, it wasn't wise of you to give her any cash without being prepared to not get any of it back, even if she knew you were expecting to be repaid. She will be upset to have been hit with your request if she thought it was a gift.

Looks like you have lost a friend, I'm sorry to say, either way

Mmmm. You could perhaps say that you are concerned- always a good word- by her reaction and ask her if she is expecting you to just give her the money?

You are being unreasonable to have lent her money without a firm repayment plan. Saying she can pay back when she 'could' is too vague. From the sounds of it she's a disaster financially and probably will never be able to pay you back.

Yes, she shouldn't be going on holiday while in debt but you knew she was financially irresponsible when you gave her the money.

Don't give her another penny, no matter how sad her story is.

Oh FFS whether she intended to pay back the OP or not she will have certainly given that impression when she asked to borrow it.

The words borrow and/or lend will have been used along with a promise to pay the money back.

What she won't have said is 'give me some money to get me out of a financial hole and as soon as I get back on my feet I'm going to spend spend spend on holidays and house plants' and be all guilt trippy and sulky when the OP suggested she start to repay.

The 'friend' is a cheeky fucker.

Hmm, you’ll either never see the money, or she’ll drop you as a friend if she does reluctantly pay.
Were you totally clear that the money were loans?

Your friend fleeced you, but you should have also requested something more specific than “when she can”.

Also pets are a luxury, if you can’t afford them you can’t have them.

This.