You should try this now. Now. Go. Do it.
Restaurant.com offers gift certificates for restaurants organized by distance from an address you enter at a fraction of the price. For example, most places offer $25 certificates for $10 and $10 certificates for $4. The added bonus is that various coupon codes work for an additional discount. Try using "SUPPER" for an additional 80% (get a $25 certficate for $3!!) or "ALL" for 50% off.
Many of the restaurants listed are not hugely popular yet or are smaller, therefore trying to drive business. Be sure to read the exceptions, too, because some of these are not valid on weekends or maybe dinners. Some also have minimums that won't include alcoholic drinks. The REAL deals come in when you find new additions for restaurants you already love.
What do I look out for? I look for higher-end restaurants (French, tapas, sushi) located in downtown areas where you know you'll already spend at least $50 for 2 people. It sounds high, but if you include an appetizer or a dessert for a special occasion, it's really easy to get there.
BON APETIT!
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