What is a lot of money to spend on......
a Cup of coffee? $3.00 Disclaimer: I'm not a coffee drinker but I'll occasionally treat myself to a milkshake, I mean frappuccino, from Starbucks which usually run $5 but that's only once every couple weeks.
a pair of jeans? $50. I usually can get my favorite Levi's style on sale around $36.
a pair of shoes? Sneakers? $45 but dress shoes that'll last? $150
Dinner (per person)? $50
Vacation? That depends on that vacation because "a lot" for a closer or shorter vacation can be an incredibly cheap international trip. Overall and all in for a two week vacation, I would be mad if I spent more than $3,000.
A new car? Trick question: one does not typically need a new car! Personally, I'd hate spending over $30,000 over a car and more likely to buy an older car and use it until I have to go full flintstones and use my feet to keep it moving. But I also take mass transit and drive sparingly.