Mixing money with family is not always a great idea. While helping out family members, if you’re in a better financial situation, is normal, if someone steps on your tail, all bets are off. You try to do a good deed, but sometimes it backfires in the most unexpected ways. It’s like lending your favorite shirt and getting it back with coffee stains and missing buttons.

This is what the original poster (who we’ll just call Alex, for the sake of this story) had to learn the hard way, after gifting his parents his car, only to find out they gave it to their jobless son.

More info: Reddit

Man gives his cars to his parents when he upgrades, wants them to have a safe ride, they give them to their 30-year-old son to sell for cash as he is jobless

Image credits: Brooke Winters (not the actual photo)

The man says his parents have a soft spot for his fully-capable brother who can take care of himself and even went to university but was never able to hold down a real job

Image credits: Christian Bowen (not the actual photo)

The man gifts his parents a full-option Jeep he could have easily sold for $9k, they use it for 6 months but later give it to his brother who sells it for a huge profit

Image credits: Karolina Kaboompics (not the actual photo)

The man buys another new car and tells his parents that the only way he would give his old one to them is if they agree to not sell it in the next 5 years, but they refuse

Image credit: u/Ok_Reply2477

The man sells his truck for $27k and uses the money to buy a new car, but his dad gets angry when he doesn’t receive his old one like he usually does

Alex was a financially stable guy with a habit of upgrading his car every few years. Instead of trading in his old but still perfectly good cars, Alex would sell them to his parents for a symbolic $1. A sweet deal, right? The idea was to make sure his folks had a reliable ride without having to deal with any maintenance issues. The latest hand-me-down was a loaded Jeep Patriot, which Alex could’ve easily sold for a cool $9,000 but chose family over cash.

Here’s where things get interesting. Alex’s brother, who we’ll randomly name Mike, had a bit of a reputation. At 30 years old, Mike’s career trajectory had been a series of short-lived gigs, all requiring a name tag and a hat, despite his university degree. The parents, who had a bit of a soft spot for Mike, gave him the car Alex had given them, which was a truck in very good condition.

So, what did Mike do when his parents handed over the Jeep? He sold it. Not just for a few bucks, but for a whopping $12,000! While Alex’s intention was for his parents to enjoy a hassle-free vehicle, Mike saw dollar signs and seized the opportunity. Alex was somewhat annoyed. After all, he could’ve pocketed that cash himself, but he chose not to sell the truck and give it to his folks instead.

After a while, Alex was ready to upgrade again, this time to a shiny new Bronco. Before handing over his current ride to his parents, Alex proposed a deal: if the parents sold the truck within the next five years, they had to sell it back to Alex for $1. Seems fair, right? Especially given the Jeep Patriot fiasco.

But the parents weren’t thrilled about the deal, feeling insulted, like Alex was treating them as if they couldn’t be trusted. “They said that I was treating them like children and that once it was their truck, they could do whatever they wanted,” Alex recalls. Taking the high road, Alex agreed it was fair, but instead of handing over the truck, this time he sold it privately for $27,000 and used the money for the new Bronco.

Image credits: prostooleh (not the actual photo)

When Alex’s dad saw the Bronco, he naturally asked about the old truck. The response? “I sold it.” So, the parents were stuck driving an old Kia, and they were not at all happy about it. They accused Alex of going back on his word, but he never actually made any promises, only an offer which his folks didn’t accept. He wanted to show his parents that they shouldn’t take advantage of his generosity, by setting boundaries.

When family members start expecting your help instead of asking for it, it might be time to set some healthy financial boundaries. Let’s be honest, nobody wants to feel like their family’s personal ATM. If your generosity keeps getting taken for granted, it can lead to some serious frustration and resentment.

Experts say that giving financial support should be a choice, not an obligation. Breaking the cycle of financial dependency can actually bring about positive changes. “Maybe by saying ‘no’, you can break the cycle of their dependency on you. Alternately, by saying ‘no’, you might help your relative/friend face some ‘hard truths’ about their financial situation,” experts explain.

If you want to keep both your wallet and your relationships in good shape, setting clear boundaries and sticking to them is the way to go. And Alex did just that when he offered his car to his parents with the condition that they couldn’t sell it for at least five years. He wanted to make sure they had a safe ride and stop them from enabling his 30-year-old, fully-capable brother.

While it might seem like unconditional support is the best way to help your kids, it can actually lead to a sense of entitlement. Parents often aim to reduce their child’s stress or make their life easier, but this well-meaning support can backfire.

Experts emphasize that putting an end to the cycle of enabling grown children is crucial, so they don’t miss out on learning to deal with life on their own. Take Alex’s situation, for example. His parents kept supporting their 30-year-old son, even though he was perfectly capable of standing on his own two feet.

So, what’s the verdict here? Was Alex wrong for setting conditions to protect his generosity, or were his parents and Mike at fault for taking advantage? Share your thoughts and weirdest family stories in the comments!

Netizens side with the man saying he’s not the jerk for refusing to give his car to his parents after they gave the other one to his brother to sell

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