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    Don’t Let Your Friendship Go Broke: A Guide to Helping (Without Enabling)

    Alright, buckle up, because things are about to get a little… loanly. We’ve all been there, right? That friend who seems to be drowning in a sea of cash flow problems, yet somehow manages to stay afloat in luxury vehicles (because apparently, debt doesn’t discriminate against luxury vehicles!). This isn’t your typical “should I lend money?” story, though. This is a tale of friendship, finances, and the fine line between lending a helping hand and getting dragged under with them. So, grab a metaphorical life preserver and let’s dive into the murky waters of financial woes!

    Yo omgsogd,

    Hello from Singapore!My friend who owns a popular restaurant has money troubles. After 20 years of friendship, he felt bad asking me for a loan, but I lent him $10,000 because I'm doing well. Six months later, he's even more in debt and feeling suicidal!Here's the thing: he has a wife, a young daughter, a condo (with a mortgage), two cars (including a Porsche!), and gold jewelry. It seems like he might be spending more than he earns, even though I live simply. Should I lend him more money?


    Hey there, friend-zone fixer upper! Ever had a buddy who seems perpetually stuck in a financial sinkhole, despite outward appearances of flashy cars and chunky gold chains? Yeah, it’s a confusing situation. One minute they’re confessing their cash flow woes, the next they’re rocking luxury goods (seriously, who needs two cars when you’re drowning in debt?). So, what’s a good friend to do? Let’s dive in, with a healthy dose of tough love and a sprinkle of financial wisdom.


    • Recognize the emotional toll financial problems can take on your friend.
    • Open communication is key. Listen without judgment and understand the root of the problem.
    • Consider alternatives to lending money. There might be better solutions like budgeting, debt consolidation, or finding a financial advisor.
    • Set boundaries. It’s okay to say “no” to a loan if you’re uncomfortable. A true friend will understand.
    • Don’t enable bad spending habits. Encourage responsible financial choices.
    Can he sell away his gold chains, at least?

    First, acknowledge the struggle. It sounds like your friend finally admitted their financial woes, which is a big step! Pat them on the back (metaphorically, unless they’re feeling super open) and let them know you’re there to listen. Sometimes, just having a sounding board can be a huge relief.

    Second, dig deeper (but gently). Okay, the Porsche might seem contradictory. Here’s the thing: some people cope with stress by throwing money at problems (or shiny new cars). Before you pull out your checkbook, have a conversation. What’s causing the cash flow crunch? Are there hidden expenses, a drop in business, or some lifestyle choices that might need adjusting?

    Third, think “empowerment” over “enablement.” You loaned your friend some money, which shows you’re a great friend. But throwing more cash at a problem with no plan is like plugging a leaky dam with bubblegum. Instead, offer to help them create a budget, explore debt-reduction strategies, or even connect them with a financial advisor (seriously, those guys are worth their weight in gold chains… minus the actual gold chains).

    Fourth, boundaries are your BFF. You have a good life, and that’s awesome! But it’s okay to say “no” to another loan if you’re uncomfortable. A true friend will understand you’re looking out for their (and your) best interests in the long run.

    Now, let’s talk about the cars.

    Selling a car might not be the most comfortable option, but it could free up a significant chunk of cash for debt repayment. It’s a tough call, but sometimes tough choices are the key to a brighter financial future.

    Next, let’s talk about his condo

    Selling a condo he recently bought can be tricky, but it’s definitely possible. Here’s the thing to consider:

    Seller’s Stamp Duty (SSD): In Singapore, there’s a tax called Seller’s Stamp Duty (SSD) that applies if you sell your condo within three years of buying it. The amount you pay depends on how long you’ve owned it (it gets lower the longer you hold onto it). Check with the Inland Revenue Authority of Singapore (IRAS) to see if you’d be liable for SSD if you sell now.

    Financial Situation: Selling might not be the best option if your friend needs a place to live immediately. Renting could be a temporary solution while he figures out his finances.

    Market Conditions: Selling a condo quickly can be tough depending on the current market. Researching similar condo sales in his area will help determine a realistic selling price and timeframe.

    Alternatives to Selling: Perhaps renting out the condo could generate some income to help with cash flow problems. This could be a good option if the rental market is strong.

    Here’s the bottom line: Selling a recently bought condo has its complexities, especially with the SSD. It’s important to weigh the pros and cons, considering the potential tax implications, finding a new place to live, and navigating the current market.

    Your friend’s situation isn’t a reflection on you. You’ve built a secure life, and that’s something to be proud of!

    Support your friend emotionally, but encourage them to take control of their finances. There are tons of free resources available online and through community organizations. Offer to be their cheerleader as they navigate this challenge, but remember, you can’t solve their problems with just your wallet.

    Sometimes, a fresh perspective can work wonders. Suggest your friend consider a side hustle…like Grab… to bring in some extra income. Who knows, maybe they have a hidden talent for dog walking or crafting artisanal avocado toast (it’s a thing, apparently).

    All those luxuries, yet he wanna borrow from you?

    Signs Your Friend Might Need More Than a Loan

    While your friend’s situation is unique, there are some recent events that highlight the importance of open communication and seeking help during financial difficulties.

    • Mental Health and Financial Strain: A recent study by the National Institute of Mental Health (NIMH) found a strong link between financial problems and an increased risk of depression and suicidal thoughts. This underscores the importance of addressing the emotional toll of financial stress, alongside practical solutions.
    • Rising Inflation: In many countries, inflation is at a multi-year high, putting a strain on household budgets. This can lead to situations where people who were previously comfortable financially start experiencing cash flow problems.

    Resources for Your Friend:

    • Financial Advisors: As mentioned in the article, a financial advisor can provide personalized guidance on managing debt, creating a budget, and exploring options like selling or renting a property. The National Association of Personal Financial Advisors (NAPFA) is a good resource for finding a qualified advisor in your area (
    • Mental Health Hotlines: If your friend is feeling overwhelmed or suicidal, encourage them to reach out for help. There are confidential hotlines available 24/7 that can provide support and resources. You can find a list of hotlines by country here:

    By acknowledging the emotional and financial challenges your friend is facing, and by offering support and resources, you can be a true friend during this difficult time.

    A true friend is there for you through thick and thin, but that doesn’t mean you have to become their personal ATM. Sometimes, the best way to help is to be a financial wingman, not a wingman who gets clipped by their friend’s financial turbulence. So, navigate this situation with care, and remember, a healthy friendship shouldn’t leave you feeling broke in more ways than one.

    The images accompanying this article were created using Leonardo, unless stated otherwise.

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