Every now and again its fun to get your friends together and go out to dinner. It's not quite so much fun if the bill comes out sky-high. There are many options for eating out without breaking the bank.
When it comes to organizing a night out, planning ahead is always a good thing. If you and your friends know what area you're going to be in, do a quick search to see what restaurants are in the area. I frequently use sites like yelp.com to check what customers say about the service, food, and value of local restaurants. As a general rule, try to avoid restaurants that are in the middle of tourist areas. The restaurants at Quincy Market are good, but they charge considerably more for their food because they are in a high-volume tourist area where those from out-of-town will buy a meal at almost any price. Even the McDonald's that is a ten-minute walk from the Faneuil Hall area is cheaper than their franchise which is right by the tourist attraction.
Another way to shave a couple bucks off your tab is to watch what exactly you're ordering. If you're ordering a dish with meat in it, be aware of what exactly comes in it. Anything that uses veal or seafood is almost always more expensive. If you don't absolutely have to have the veal parmesean or the shrimp scampi, get something else. Also, be aware of what you're drinking. Some places don't offer free refills and only note the fact on the back of their menu in small print. When in doubt just have water (which is better for you anyways). I typically save some money by getting something for take-out and having a drink with me so I don't need to buy one. Partaking in alcohol consumption is also very expensive at restaurants and bars. If you need a drink wherever you happen to be, watch out for drink menus that don't list their prices! I had a friend who ordered a margarita at a restaurant once and there was no price listed - for that one drink they charged her $15!!
When walking around an area looking for somewhere to eat, I recommend watching both the number of people and the demographics of those people, especially the age. As a general rule, if there are a lot of people in a restaurant there can be several things going on: it's in a tourist area, it's well-advertised or popular, and/or it's really good. If you're not in a major tourist area or if you've never heard of the place and it's crowded, it's almost certainly good. Then look at the age of the people in the restaurant. If you're looking for a good value in a restaurant, you should look for college-age people as well as elderly people in casual wear. The casual wear is important because that means that the restaurant isn't just one that they would go to on a special occassion. Many elderly people also tend to be penny-pinchers for various reasons so if many congregate in a restaurant on a weeknight, you can almost be assured it's a good value.
A quick word of warning: if you see prices listed outside a restaurant that seem too good to be true, they very well might be. I personally have been to a place that advertised a $5.25 lunch special only to regret eating the food as it made me sick afterwards. That said I have been to other places and gotten lunch at even lower prices than that and they were absolutely fine. Use your best judgement. Generally, if there are a lot of people there, especially ones that look like they go there almost everyday, then you would probably be fine eating there.
If you really want to go to a nicer restaurant that you know is a little more pricey, try going at lunch instead of dinner. At lunch, restaurants will typically serve smaller portions of the same food they do at dinner and at a smaller price tag.
**menu picture used under Creative Commons - http://www.flickr.com/photos/ataradrac/4539297682/

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