it depends more on what the person's other habits are that coincide with things like tipping. I tip at 5o% a lot of the time, and I'm good with money. It's not a bad habit to tip well, and it's not something someone else can say is wrong because it's a choice made. You can tip someone well and then just not blow your money on stupid things.
Say he tips half on a 4o ticket. Let's say the ten bucks that would be standard is accounted for, there's ten bucks left. If you want to balance that out, spend ten less dollars on crap you don't really need but are more than likely to buy. If that means one less woman doesn't get a drink at a club, that's his choice.