Don't think that you can't get around on very little money. There are few cities that don't have inexpensive restaurants or deals that can be used to go out for a meal. There are lots of things that can be done for free or very little money. Cinemas are often cheaper during the week and lunchtimes in fancy restaurants do good deals.
Pack a picnic in the park - there are free and using a proper basket, linen napkins and cutlery instead of paper ones will make the simplest of food seem more expensive and chic.
Investigate what public facilities have to offer - free lecturers, or concerts, reasonably priced venues and events in your own area and you will have fabulous interesting things to do which will encourage you to do more and find more ways to have fun on little money.
First nights of plays are often cheaper, are there magazines that want people to review events in return for a ticket?
Thinking outside of the box - and again what seems to be the buzz word running through this blog - IMAGINATION!!