I don't tend to spend big money on one-off events like concerts or sporting events (or even generally on lots of vacations/holidays), preferring to spend on items I can use many times. The exception to this rule are restaurants, and I've been known to run some up big bills there. But I don't think that quite falls under the spirit of the thread.
Opposite here ~ for the last couple of years we've had events/trips away as birthday/Christmas pressies. We've done Les Mis in the West End, Waiting for Godot with Patrick Stewart, and Bill Bailley live. The tickets, the transport and the accommodation do add up but I consider the excitement of the build up, the planning of the trip and the memories to be invaluable ~ especially with a great friend who you don't see that often. Oh and the gigs were good too ~ forgot about The Main Event! And things like this you only kick yourself if you miss. Money is for enjoying.
The last sentence I can wholeheartedly agree with... I just feel a slight sense of waste when I spend it on one-offs. When I spend it on indulgences that last a while I don't have that sense. For instance, I suspect few on the board spend what I do on clothes, but for me it's not excessive because I get to enjoy them for the many years that they last. Whereas a holiday would be over in a couple of weeks.
What's definitely important is enjoying it, though! And that just varies for different people.