I hope that I've been clear about how cheap I am. If I haven't, this post might set the record straight. So here's my guide to eating out on the cheap...
First off, head for the big meal at lunch if you can. Not only are the meals cheaper, sometimes half price, but it's more healthy as you can work off the calories through the rest of the day.
Second, pick up an Entertainment Book. There are a few buy one get one free dinner places in the Boston area. Use up one or two of those (depending on when you buy the book) coupons and you have made your money back.
Divide your portions. Usually restaurants give you enough food for more than one meal. Sometimes it's just enough for a snack later. However, at a place like the Olive Garden, with free unlimited salad and breadsticks, I end up taking 85% of my main course home.
Save the alcohol for home. Not only do you not have to worry about drinking and driving, but the wine makes a nice nightcap with a loved one when you get back. At a number of places, this alone will save you upwards of $20 on the meal.
A last thing you could do is buy gift cards at a drug store with your high reward credit card. I think it would qualify for 5% cash back with most cards.
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