Oh, I see! You are going a little "old skool" with this, and you tell each other, to make a little expectation.
What to do on a date
Have you tried geocaching? You don't need the expensive GPS units to find them, i literally started out just getting the coordinates, plugging those into google maps and then using street view or pictures on the geocaching website to aid me in where to look (this can take away some of the fun factor but for starting out and not know what in the world to look for it was a big help). Best part is it is free! You don't have to take anything from the cache or sign the log but just going and finding them is an adventure in itself and some alone time with your SO is always wonderful. It is actually how i met my fiancee!
As for something cheap but still fun, thrifting is always a blast due to the nature of wandering through flea markets, antique malls, and thrift stores and seeing what you can find. To make it even more fun try doing a $5 challenge and see who can find the coolest thing for that amount. You don't necessarily have to buy it but just saying that you found a metal rose or hand painted egg from china (with certification!) is pretty darn cool! Some friendly competition is always nice. Once again you and your SO get to spend time together looking at some very off the wall stuff and might find something really cool along the way!
LazyG made a good point. There were things you could have done better, I'm sure there were things he could have done better.
As far as making it up to him, if my girl took me out on a date, that would mean a lot, because it almost never happens. It's happened twice in 25 years. So that would be really special to me.
What to do on a date
You could do a scavenger hunt of small items, online scrapbook of your relationship, or get creative (paint, write, whatever.) Just from the fact you're seeking out advice, I think that the effort will be there and it really is the thought that counts :)