The Red Dining Book (LA/NY +)

The basics; You buy this little book for $115. It has a bunch (27ish) of restaurants in it. During the calendar year, you bring the book to each restaurant, order 2 entrees, get the cheaper one free, and they put a big ol' stamp in your book.

The fun; it's like you're on a year-long scavenger hunt but without running or solving riddles and what you're finding is delicious food. You have a year's worth of fun date ideas, get to try a bunch of great places you maybe otherwise wouldn't have, save WAY more money than you paid for the book, and the people at the restaurants are delighted to see you because they think the book and the book people are whimsical and fun because IT IS AND YOU ARE.