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The question: I have a friend who I've known almost my whole life. A while ago, he asked me to wire him money because he "lost his wallet" – and not a small amount. Then he dropped out of sight. It turns out his life was nosediving because of alcohol and he wound up homeless. Now he's getting back on his feet again. I'm happy for him, but now I'm unemployed and want my money back. How do I approach him?

The answer: There is some wisdom in the old adage that money and friends don't mix. More often than not, mixing the two can create rifts in a friendship and add an awkwardness that wasn't there before.

Now, in your situation, you did what a good friend does – in fact what a great friend does: You supported your friend when he needed it. Although you later realized that he was struggling with substance use and likely myriad other difficulties, you put your trust in him and gave when you thought he needed it.

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It is your friend's turn to now support you. The best way to approach him is clearly and directly.

Here are some tips you can follow when making your request:

Describe the past situation: "You may remember that in [month/year] I lent you [x dollars] when you had called and let me know that you lost your wallet. I really wanted to help you out, so was happy to do so. I know you've gone through a lot since that time, and I am really happy that you are getting back on your feet again."

Describe your current situation (not necessary but it may help to give context): "Unfortunately, I recently lost my job and am struggling financially."

Make your request (be specific, and provide timelines): "So, I need the full amount of what I lent you back, ideally by the end of the month."

Be reasonably flexible and allow your friend to respond: "I realize that this is likely not something you were planning for. What are your thoughts on being able to get the full amount back to me within that time period?"

Then negotiate a reasonable resolution that is acceptable to both of you. Be specific. Ask yourself what you are willing to accept and convey that clearly to your friend. For example, if you need the money within the month and he proposes to pay you six months down the road, let him know that won't work for you and why. Tell him that you do not want money to get in the way of your friendship and that you are hopeful you can arrive at a resolution that works for both of you. Do not apologize (as that dilutes the request) and do not be overly wordy.

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If your friend is not willing to give your money back or work to get it to you within the limits he has, unfortunately, it may be that you just have to learn a very valuable lesson from this and decide how, or in what capacity, you want to keep this friend in your life moving forward.

Send psychologist Joti Samra your questions at psychologist@globeandmail.com. She will answer select questions, which could appear in The Globe and Mail and/or on The Globe and Mail web site. Your name will not be published if your question is chosen.

The content provided in The Globe and Mail's Ask a Health Expert centre is for information purposes only and is neither intended to be relied upon nor to be a substitute for professional medical advice, diagnosis or treatment.

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