I like how there have been an almost equal amount of serious and funny replies. My wife and I have been together over 15 years this year. We have spent a portion of many a road trip day-dreaming about winning a big lottery. Here's what we would do:
1. Make everyone in our lives rich. What's the point of being rich if your family and friends aren't either? Say we walk with 500 million from the PB on Wednesday, we'd easily give away 200 million or 40% to family and friends. I don't want to have to pay for them to come stay the month in Hawaii with us. I want everyone who has shaped us, supported us, or put up with us to be financially free. No jobs for anyone!
2. I'm not a car guy, but after buying two armored tanks to drink my two precious little boys around in, I'd buy a 67 Ford Mustang Fastback. I rode in one as a teenager and told myself I'd get one if I ever hit it "big."
3. Upgrade our house in Colorado, but also buy two more properties. One would be a fancy downtown Chicago condo. 3-4 bedrooms with a wine cellar. We would use it for all of the Bears games with our family and friends. We'd also buy the rights to six PSLs. Other property is to be determined. After travelling extensively the next several years, we will find a huge lakehouse on a huge lake. Something with a big dock, sand pit, wrap around porch and lots of privacy and fishing. This is where I will retire.
4. First trip/vacation? Las Vegas. I would invite my two older working stiff brothers to the Eiffel Tower restaurant while my wife has a girls night out with her friends. I would wine and dine them to their amusement and bewilderment with fancy French food and seriously expensive Bordeaux. Once dessert arrived, I would tell them to feel under the table. They would find and then open an envelope with a check with too many 0's. They would cry. Then we would take a private limo filled with the finest sativa I can find to a strip club and make it fucking rain. Sorry, honey. I wonder what 50K cash could get my divorced brothers at the Spearmint Rhino?
5. After initial dole outs of money and preliminary vacations, we'd go back to school. Maybe I'd get a Masters or a Bachelors in another field.