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My brother won't pay back the loan we gave him

The question

My husband and I lent my brother a large sum on our line of credit. He lives out of province and his assets are tied up in his fast-growing, successful business. He needed funds to bridge him until the sale of his home. He was to pay us back immediately after the house closed last April. But he has blown us off for months, most recently promising to repay in the "near future" following some important business transactions. I gently told him that blowing us off is totally not cool, and he apologized – but there's still no concrete suggestion as to when he'll pay up. He has a nice lifestyle, and it's not our job to keep him afloat. I've been patient, but I'm concerned, feeling a little hurt and losing sleep. My husband is relaxed and trusts everything will work out. How can I tackle this with my brother?

The answer

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That would make me completely bat-guano crazy.

I hate being owed money under the best of circumstances. It gnaws at me. It preys on my mind.

But if it was my brother; it was a substantial sum; I had to borrow it to give it to him; he'd given me a deadline but failed to pay; he wouldn't say when he would pay; he lived far away; was blowing me off; and had a booming business and a high-flying lifestyle? I wouldn't be able to sleep, either. I'd try, but my eyes would be popping open at 4 in the morning, and on the ceiling I'd see filmic images of him in a hot tub, gold chains on his chest, sipping mimosas, smoking Cohibas as his butler serves him Lobster Thermidor on a silver charger.

I'd be tempted to leap out of bed, fly to wherever he's holed up, kick in the door, grab him by the lapels – or maybe his nipples – and scream, spraying spittle in his face like a theatre actor: "You bastard, unless you want me to stick your head in the toilet like I did when we were kids, before bashing your head in with a pipe wrench, give me my freaking money! Plus interest and expenses for coming out here!"

Just so we're clear: I'm not telling you to do that. I'd be drummed out of the advice columnists union. It's just my way of saying I sympathize.

As to what you should do: I'd say take a page from your husband's playbook and stay calm and positive, even chilled and bubbly (like the Dom Pérignon your brother's probably swilling as we speak – sorry, I'll stop). Don't get passive, though. You need to be all over this slippery sibling like hot fudge on a sundae.

Pepper him with phone calls and e-mails. Always be friendly: A deadbeat dude like this could use an angry exchange as further excuse not to pay. But show him you mean business – that, in the matter of your money, you "mean to prevail" (to use Gore Vidal's excellent phrase).

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Refer to it as "my money" as much as possible. You know how, when a kid's taken hostage in TV shows and the movies, the cop tells the parents to keep using their kid's name in negotiations so the hostage-taker will see the kid as human? Similar principle. Your brother is holding your money hostage, and the longer it remains in his possession, the more it will seem to him like it is his money, and less like your money.

Emphasize the fact you had to borrow to lend to him. Lines of credit are wonderful, but banks are serious about repayment. They "mean to prevail" when it comes to "their" money.

You could lose your house. Even if you're not in imminent danger of that, it has to be an eventuality because you added to a loan against your house. So play that up. He'd have to have a heart of stone not to pay you back if he thought it meant you and your husband might wind up snuggling in a refrigerator box.

And I don't think you'd be out of line to recruit your husband and other relatives to turn up the heat a bit.

One other idea: If he truly is cash-strapped, tell him you'll take your repayment in the form of shares in his company. If his company's growing as fast as you say, this could be the best money you ever lent. But don't take shares until you do your due diligence: His money issues may indicate that his company isn't doing as well as it appears.

And going forward, promise me: In the interest of your health, well-being and peaceful night's rest, you're never again going to lend money to anyone, ever – especially not money you can't afford to kiss goodbye with a shrug and smile.

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