“Dear Cat, When my friend lost her job and was struggling I lent her £1000 on the basis she’d pay me back within a year. Me and my husband had saved the money for 3 years so we could go on our dream holiday to Florida. It’s now been 18 months and even though I’ve dropped hints about paying me back she’s obviously avoiding it.

She’s now working again but with two kids she must struggle. That said, I think she wastes money – she recently bought an expensive phone for her kid when a cheap one would do. Should I demand my money back and risk putting my friend into further debt or cancel the holiday we’ve been planning for so long?    Thanks, Jenni.”

Dear Jenni, thanks for your question.

In my opinion the key to this dilemma is honest communication.  Both of you will be feeling certain emotions around this issue.  You are feeling used and you are starting to judge your friend for ‘wasting money’; you may also be questioning whether yours is a true friendship because she has failed to keep her promise, and pay you back.

You friend may be feeling anxious in other ways.  For some reason she is not displaying the confidence required to discuss the loan and the return of the money. She might be telling herself that perhaps you are ‘well-off’ enough not to need to money yet (as you are only dropping hints), or she might feel particularly awkward about discussing how and when to pay it back, so she is avoiding it completely.

You first of all need to find the confidence to address the issue.   Disagreements about money are one of the most common reasons why relationships of any kind run into trouble; it is easy to link money to whether someone cares about us or not, and therefore money is hard to talk about.  My feeling is that if you got to the point where you cancelled your holiday, rather than address this issue, then your resentment would be so great that your friendship would effectively be over.

My suggestion would be to write down what you would like to get across to your friend, and speak it out loud to yourself to hear how it sounds.  Always start with positive things first, and always use “I” statements, such as “I feel…”, rather than “You are making me feel…” because as soon as the other person feels criticised, they will defend themselves and the conversation will become an argument.     An example would be “I need to talk to you about something. I really care about you and worry about you, which is why I leant you the money a year ago, but I need it back now, and we need to talk about how that is going to happen.”

Avoid getting into a discussion about why you need it back, that is not the point.  You did a kind thing by lending the money in the first place, and you have every right to now, kindly, ask for it back.

Depending on how your friend responds, you may need to ask yourself how much this friendship matters to you.  Is this a very unusual blip in your friendship, or have you felt ‘used’ and undervalued by this friend before?  You will need to decide how reasonable you are going to be about this issue.  If your friend starts to argue and ‘fight back’ then this may show she is not as concerned as you are about keeping things pleasant, and therefore is not as concern as you are about your friendship.  She might be prepared to lose you as a friend, in order to try to avoid paying back the money.