This post isn't about not spending money on entertainment, it's about maximizing the money you do spend on entertainment.
I've been a big fan of the Entertainment.com coupon book for years now. It has always paid for itself many times over. Of course this means you are spending money, which doesn't sound very Mustachian, but even MMM sets aside about $50 a month for restaurants. So this is based on the notion that you spend some money on eating out and other forms of recreation. Here is a way to stretch that dollar further.
The Entertainment.com Book Coupon Savings Book (ECB), for those who haven't seen one, is a very thick book of coupons that typically offer 2 for 1 entrees or attractions at restaurants and entertainment venues (sporting events, local theaters, golf courses, etc.). It comes out around Labor Day in the Richmond VA area (I presume the same for other locations) and retails for $35. The coupons are good until November 1 of the following year, a 14 month window.
So here is how to game the book.
1. Do NOT buy the book when it is released. As the months go by the ECB will get discounted more and more heavily as it gets closer to the next release date. By Christmas the book is often on sale for $20. By March or April it goes on sale for $10, and I have bought them as cheaply as $5 (with free shipping) as recently as a few weeks ago. So there may be a window between Nov 1 and late winter or even late spring when this is not at your disposal, so think about it as a seasonal event.
2. Get a Mustachian Buddy (or a big spender, or anyone that likes saving money this way) and buy books together. Then coupon swap. There are restaurants that my wife like to frequent multiple times, your friends will have the same. This essentially doubles or triples your book for your favorite haunts.
3. Avoid the pricier restaurants in the front of the book unless you go there already. You might have an offer saving you $20 off an entree and still walk away with a $60 bill.
4. Look for the inexpensive restaurants, especially your favorite haunts. There is a Jamaican restaurant near us that has a $9 coupon. Two entrees, two drinks, tax and tip (based on what you would have spent without the coupon, don't be a dick to your waitress) sets us back about $15 instead of the $23 we would have spent. $15 is a pretty cheap date night, and the savings were closer to 35% vs. the 25% in the example above. Cheaper still if you prefer water, but we typically get soda or tea. With coupon swapping and multiple books we can go here four times a year for the same price as that $60 swanky place and have just as good a time and enjoy really good food.
5. Be sure to look at the various coupons to other non-restaurants. In our book there are three coupons for Dicks Sporting Goods - $10 of $50, $15 off $75, and $20 off $100. I frequent Dicks at least a few times a year and we buy our athletic shoes there, so this is just a no-brainer. It was money we were going to spend anyway, now we don't spend as much.
6. (Edit) Also, you can print discounts from their website after you register the book. And do register the book, they will let you know via email when they are selling the book on sale. The coupons you print typically are only good for a few weeks after you print them, so don't print until you know you are going.
7. Don't go out just because you have a coupon! Go out because you had planned to go out in the first place - just do it cheaper.
8. And most importantly, keep the book in your car. There WILL be a time when you want to eat on the spur of the moment while out and about and it doesn't help you sitting on your bookshelf at home.