40 Free Date Ideas You'll Both Love - I've seen a lot of date idea lists and I actually liked this one a lot more than others I've seen.
This was one of the easiest and most well-recieved gifts I have ever given. Spray paint popsicle sticks to represent different categories of dates (Requires Planning, Go Out- Little to No Money, Go Out- Money, Stay In- Little to No Money, Stay In- Money are the categories I used) and then write the dates on each stick. Draw a stick when you want to have a date. Simple as that.