I have the best co-worker for stories like these, I'll have to pick just a few...
I work in an organisation where salaries are set by level and years, so this co-worker is on my level (we earn very decent salaries for our city) and is always running out of money, even complaining when he pre-pays visas of $50 and has to wait a week for reimbursement. He drives a nice audi a4 which I know is financed, but after a new audi dealership opens up, we go check out the new R8 on display. While there a sleazy salesman tries to sell him an A5. I tolerate the salesman because I'm sure my in debt co-worker isn't dumb enough to fall for the "almost exactly the same payment as your A4" schpeel.
A few days later he tells me he loves that car. After I try talk him out of it, but then he says he actually bought it that morning.
Now here's where it gets interesting. I do a blog post on this purchase (http://investorchallenge.co.za/your-car-doesnt-cost-you-r5800-pm-it-costs-you-a-million-dollars-you-fool/
if you want the whole story). It gets a great response, but due to all the shares, the said coworker also finds it. He's not happy with me, and we barely speak for another year.
Fast forward a year later, and we're friends again, but what do I see in the basement but a brand new audi S3. Guess who it belongs to. A few days later, he says he notices my electric bike parked in the basement and says he wishes he had one so he could save on fuel!!!
Then a week later, he says they've decided to buy a new property, just outside the city (a 35 mile commute), and they're going to build their dream house there. Begins telling me how he'll be able to control the lights from his ipad etc, and they've already bought kayaks for the whole family as it has a lake on it.
If that wasn't bad enough, he has a private pilots licence, so when they go to see the property he drives 15 miles the other way, rents an aircraft and flies to the site (in an estate with an airstrip) for a couple of hours then flies back.
I've given up giving him financial advice...