I'll admit it, even I like to go out for dinner every once in a while. I deserve to treat myself for all of my hard work and you should too. But, there are smart dining options and options that shall we say, are not as wise.
First off, I can't stand fancy restaurants. If I have to put on a suit and tie just to eat food, I will not go. I remember once I was in New Orleans for a conference and was forced to wear a blazer because that was the restaurant's policy. Had I known this prior to arriving, I probably would have chosen a different restaurant. When an establishment does have a policy of that nature, you can also bet that it's going to be an expensive outing.
There are special occasion restaurants, which I may visit once or twice a year to celebrate something truly monumental. If you land your dream job, get a raise or are celebrating a special occasion, then it's okay to reward yourself with a $50 steak. But that is the ONLY time I will give you permission to order anything that expensive.
Many moderately priced restaurants are just as good as more expensive options. In fact, price doesn't always determine quality. A few weeks ago, I was at a very high end steakhouse (a friend gave me a gift certificate for my birthday) and not only were our steaks fatty, but my guest's steak wasn't cooked properly. When I do visit a restaurant of that nature, I expect everything to be perfect. Luckily, the service was good and they remedied the issue quickly.
If you are forced to dine at a restaurant a bit out of your price comfort zone, then try to take home leftovers to justify the expense. A $50 meal, with enough leftovers for lunch the following day psychologically turns it into two $25 meals, or if you prefer, a free lunch.
And whatever you do, please don't order the $30 chicken dish. Order something that you can't make at home. Order something special...the rack of lamb perhaps, or the Chilean Sea Bass. Why waste your money on an item you can cook for a quarter of the price. Yes, the markup on food is that high. Now, do you see why cooking your own meals at home is a more responsible option?