I have a problem with spending money and have always been a very frugal person...which is strange for people my age especially.  I'm great at saving money but there are times when I go "What am I working for?  What am I saving up this money for?"  My spending style is that I live frugally but may spend a large amount (once in a blue moon) on a trip with friends or on a gaming console.

I'd love to take my parents and siblings hang gliding these holidays.  This is a once-in-a-lifetime experience (unless you can afford to do it again and again!) and I know they'll love the feeling of flying like a bird.
It's about $220 per person to fly up with for half an hour (so over $1000 in total).  I'll be paying of course.  I don't have a fantastic job but I've always been a bit of a miser (when it comes to eating out, travelling, clothing...and I don't care about fashion and I don't even plan to buy a car) so I can afford to do this.  
But am I being rash in wanting to do this?
I want my parents to experience this while they're still fit enough to.  I think about how wonderful the experience will be but then the "ifs" and "buts" start coming and I start thinking "$1000 - and for  just half an hour" and about all the other things I can get with $1000...and that's a LOT of stuff.

I'd love some pearls of wisdom.  When is it appropriate to spend a lot of money on fun/experience?  When is it wise to just stop worrying about the buts and...just enjoy and do it?

ok..
How do I join this family

I went sky diving for my 30th., for me yes its an experience that lasts a life time.. get photos and video.

are you sure that everyone in your family will enjoy hang gliding.. there may be be or two that the experience will simply be terrifying for. You dont have to tell them this is what you are planning, but be round about gauging how they might enjoy being fragile in the elements.
my son eg would not enjoy it so much.. he'd be more like yea yea.. whereas If he went shark diving his adrenalin would rush.. Id loath the very thought of shark diving and probably refuse )

Im thinking that you are typically very sensible with your money so you have not come to this lightly.. its something you want to do, thats what your money is for..
If your the kind of person that may regret the choice latter dont.

You know .. parents enjoy knowing their children are living life to the fullest as much, if not more than actually doing these things themselves.
If you think that your parents need to hand glide to get the full enjoyment out of it, think again. every new adventure my son ha, I have... so just make sure your spending the money on others to do it for the right reasons.
if it makes  fulfilled to do this for them, this is something very special you are giving yourself.
If your not doing this for you then its a waste of money..

Its not $1000 for half an hour. having an experience like this lasts for years.
I recommend that if you do have a garden party planned for afters, sharing the experience is the best part.

Thanks for your very wise and thoughtful reply, StormGirl Blue!  

So you've done something similar too with skydiving!

My dad's the type of guy who says he'll give anything a try...and although my mum is a bit hesitant about the idea, I've convinced her it'll be something she'll never forget.    
About the possibility of regretting this later on, I'm sure that I'll regret NOT doing this.

I love what you said about parents not needing to enjoy such things themselves...


My parents are exactly like that as well. But they've spent their lives watching people do these things...or seeing beautiful places on TV - and I want them to finally have these experiences for themselves.  Besides, they'd never spend such an amount of money on such a luxury so I guess I want to give them this chance.
OK, I'm going to do it.

Thanks again for your wise words!