I'm a very frugal person, so I'm having a hard time answering this question. How about: Anything bought with change? I have a jar full of 25 cent, 10 cent, $1, $2, etc. coins.. Anything in that jar is considered "free money".. Roommate needs some change? He can take some from the jar and "owe me one" later.
Everything bought with credit, bills, or my debit card, is scrutinized. I'm usually saving up money for trips, so I don't throw out money for any reason. Unless it's money from the change jar, like I said.
I
do allow myself an "entertainment budget" and a bit of a "whatever the hell I want" budget. So every month I have money to spend on random stuff, if I want to.. I usually don't, but if I do - I have money budgeted for it. So that doesn't really feel like I'm throwing money away either. Basically what ends up happening is I don't spend most of that money and it goes into savings.. and then every once in a while (every couple months?) I see something expensive that I need, and I splurge. And I don't feel bad about splurging, because I know that I'm a frugal person, and that all that money I don't spend each month adds up - allowing me to splurge. It actually feels awesome to splurge like this and not have to worry about it ruining your credit or whatever. I think it might be one of the subconscious reasons why I do all this.
When I'm on a trip, I might blow $100 on a scenic cruise, $300 on a bungy jump, or whatever. But that's all sort of budgeted too. Sort of. I basically know that I live for this stuff, so spending $1k over my budget isn't going to break me. So on my trips I'm a bit more free with how I spend money - but at the same time I am also a frugal traveller. I stay at hostels.. but I do eat out at restaurants. I'm a paradox.
All that text and I didn't really answer your question.. or maybe I did?