This would largely depend on the amount of money I had won. But say, for instance, I won EuroMillions, and the winning was £100m - easily enough to do pretty much everything I want to do. In which case...

I would procure...
...Eyes on Final Fantasy.
...a lot of things for EoFF, such as a better server, better prizes, possibly pay someone like Azar to carry out journalism for us full time, even pay for a few meetups at nice places... stuff like that.
...a nice house in or near Edinburgh.
...a nice house in or near lower England.
...a nice flat near Old Trafford.
...a nice house in California.
...a nice house in or near Hastings (NZ).
...Navah House, the house in NZ in which I grew up.
...an American visa (the $1,000,000 investment option).
...a provisional driver's licence.
...a Holden Commodore.
...a nice place for the family of the child I sponsor.
...a large investment towards saving the Jaguar.
...naturally, I would invest in other charities but I don't know which ones.
...various SE fanboy material.
...all the gaming consoles I don't already have.
...two awesome desktop computers.
...two awesome laptops.
...lots of games! I'd even get Xbox Live. Haha.
...a trip to see EoFFers around the world.
...a trip to see a few of my mates from High School.
...a trip to see the ex's I haven't met yet due to having online relationships. This might sound weird to some, but I get along with all of them, and they were important parts of my life, so it would be nice.
...trips for EoFFers to meet me and each other at my place. I miss doing this as often as I used to.
...a few holidays just for the sake of seeing the world.
...a very nice engagement ring and a very nice wedding for Danielle and myself.
...more of Mum's artwork.
...some artwork from artists at EoFF such as Pete for President, black orb, Cute&Dangerous, etc. to put up on my walls at my main home. Wherever that might end up being.
...nice food. Oh, man. I would spend a decent amount on nice food.
...gym stuff. Because of the nice food. xD
...I would give away significant sums to my closest friends, such as Dan and Lev, to aid them in things they want to do in life. The same goes for all my family. For people I know who struggle to get by despite doing what they can, I'd obviously help to get them on their feet, too. I'd probably set aside about £5m for funding friends and family (both mine and Danielle's).
...Education for myself in things I want to know about. Although probably not a degree or anything. Home-tutoring would be more my thing. Hire people to help me learn to play instruments such as the piano, help with coding EoFF stuff, help me learn to cook better (I'd probably just pay my Mum for that), help me learn languages... things like this.

I would live off the interest on around £50m, which should mean many, many thousands per month.

Once I had finished with all my travel, I would likely get back to work in some form. Be that my current job, a voluntary position somewhere or a small video game store or something, I don't know. But I don't think I would like to stop work altogether, it's something I tend to enjoy. Maybe I'd just work on EoFF full time.