Don't know if you have kids yet, but I find I like to spend money going out and doing things rather then on stuff like clothes. So to keep my spending down in this area, I've made some written and some mental list of places in the metro area that are cheap/free to take my kids to on days I'm off or on the weekends. We do a lot of picnics in various parks around town, go to the zoo, science center, etc which are all free activities around here. Plus local theatres have free movies at various times during the summer, etc.
There are a lot of other free/cheap events in our area to (if you are single or are just hanging out with a friend for the evening). Keep an eye out in your local paper, check restaurants/venues ahead of time for special deals or free periods (example The Muny, our outdoor venue that does live plays/musicals in the summer in St. Louis, has about 150 free seats in the back that they allow anyone to sit in on a first come first serve basis). Our symphony gives I think 50 free tickets away on a first come first serve basis too.
By planning ahead of time, my family has been able to do a lot of fun activities while still staying on a pretty tight entertainment budget.
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