So I have become a serious cheapskate when we eat out now. We hardly ever eat out and pay full price anymore. First it started with going out with friends to a place with 1/2 price appetizers between 5 and 7 - we get there at 6:30 and have appetizers for dinner (this includes chicken wings, which counts as real food in my book.)
My 3 best resources:
1. Restaurant.com - they have gift certificates between $10-100, although most are for $25 or $50. $25 certificates are usually $10 to $15, already saving you at least ten bucks. But here's the secret - sign up for the email list, and use the tons of coupon codes they send out. For all but the most popular restaurants, you can get them for $2 or $3 at 80% off. For Christmas, I gave Boyfriend's brother a folder full of certificates I'd picked up over the previous two months for a couple bucks each.
Caveat here: they don't expire for a long time, which means you may forget about them. I usually buy one and then when we use it I buy another. I have no shame at going to these places every two months and using a certificate every time. Also, check the fine print - some are only good if you buy $50 of food, or only Sunday through Thursday, or what have you. We have some for Ted's Montana Grill, which is a completely awesome and delicious restaurant, but you have to spend $50. It's not a terribly expensive place which means you either need four people or a hollow leg.
2. Entertainment book (entertainment.com to order) - if you've never heard of this, I feel bad for you and your wallet. These are basically just big books of coupons, which are available in most big cities, and contain offers for lots of local restaurants and other services as well as chain restaurants. My mom got me one this year and within 48 hours of receiving it we'd already gotten buy 1 get 1 free fajitas at Baja Sol. Given that the book is $20, you can pay for it pretty quickly. There are some other really good things in there, like $10 off per night through Priceline, and the usual dry cleaners and what not. But definitely worth it for the restaurants alone, especially if you're willing to try new places, because most of them are buy 1 get 1 free.
Caveats - many of these restaurants you may never have heard of. My book has a ton of little places that aren't familiar to me, and so it can be a bit of a gamble. Best to check the internet first for any reviews. Also, although many coupons are BOGO, they can limit the amount you can get free. So a Mexican place near us that we like has a BOGO coupon in the Entertainment book, but only up to $6 (most entrees are $8-9, so not a huge deal, but kind of annoying.)
3. Groupon - sign up and get an email each day with some kind of percent-off deal on a gift certificate to a specific place. They just started in my city a few weeks ago and it is somewhat hit or miss, but when it hits it's pretty awesome. For Christmas I got Boyfriend's mom a Groupon for $60 of services at an Aveda salon - and it only cost me $25. And I also got super cheap tickets to the art museum to keep in reserve if we have a slow Sunday.
Caveats - you get a random deal each day which isn't really targeted to you, so you may have no interest whatsoever. And a lot of them aren't for food (they're for, say, personal trainers) and almost none are for durable goods. But when you get something good, it's REALLY good - usually at least 40% off. And they're good for a year. On the downside, though, probably 400 other people also bought that same coupon today, so they may be a little slammed with the coupons for a month or two. They're good for a year, so I'd hang onto them for a few months so the staff doesn't give you the stink-eye.
4. Email lists of chain restaurants - I am signed up with every chain restaurant we've ever been to, and ones that we'd like to go to as well. Frequently you get something for signing up, so if we're thinking of going someplace, I try to sign up for it a couple hours beforehand and see if they send me something. Tip - they usually ask you for your birthday and sometimes your anniversary, so unless you want to eat out twice a day for the two weeks surrounding your birthday, try to space them out and choose random months. I've never actually had anyone ask me for any proof, and if you stick the coupon in with the bill, they won't sing to you either. (Blech.)
Caveat - in addition to coupons you will get lots of other emails, about special events, etc. I don't mind too much, but if you already get a lot of email you might. Perhaps a separate email address you check only when going out? Also, the coupons aren't as good - usually on the order of $5 off or a free appetizers.
My favorites: BD's Mongolian Barbecue - recently I got a "loyalty card" to print out that essentially means buy 3 get 1 free.
Red Robin - I get a free appetizer coupon every couple months.
The Melting Pot - they send you free chocolate fondue coupons for birthday and anniversary, but more importantly on their email list they let you know about upcoming special-price days.
Gordon Biersch - sometimes I get a BOGO entree coupon, which is super nice.
Any other suggestions for good sites I've missed? I love me some discounted gift certificates, so if anyone knows of sites I don't, please comment.