One thing I'm careful to work on is not being judgmental and not jumping to conclusions. For example, I used to be exasperated when I saw a "big" kid in a stroller - thinking that this kid was clearly old enough to walk and hey, maybe this is how our obesity problem started. But then I realized that I don't know that kid. I don't know the family. For all I know, that kid has a disability and can't walk. And a stroller is easier to maneuver than a wheelchair, so why not?
Sometimes, I find myself being judged on how I spend my money, and so I also work to not judge others on how they spend their money. Sure, I think that above all, you should pay your bills. If you are splurging on designer dresses but falling behind on your mortgage, I find it hard to not be exasperated at your decision. But beyond that, your money is your money and you can do with it what you want. Maybe your thing is designer clothes. I balk at designer prices, so that's definitely not my thing.
But maybe you think my spending money on half-marathons is crazy. (When I'm out running in the pouring rain, I may agree with you.) But I love the big races (especially Disney races) and while they're expensive, I have a great time doing it. I love the growing collection of race medals hanging on my wall. I also love wearing cute running gear. And I love how I feel after a great run. Do I need to spend money to have a great run? No. Do I love doing it anyway? Absolutely.
We all have different values. If you're reading a finance blog, we probably have something in common - the desire to save/spend wisely/plan for the future. But what we do in addition to that differs widely.
What do you spend your money on that others may find crazy?