I don't have an answer to your immediate question, but when you do spend it, consider finding ways to stretch it into as may fun times as possible. For example, there's a hole-in-the-wall Mexican place where my wife and I can get chips/salsa, a few a-la-carte items, and a happy hour drink each and leave spending less than $20. We enjoy the food as much as any fancy dinner, and our conversations are just as awesome there as well. We will do that every couple months, and it's well worth the 20 dollar bill.
You say you have a long list of things you'd like to do. Maybe rank them from cheapest to most expensive, and start doing the cheap ones NOW, instead of years down the road. If those cheap ones are making you feel less "uncomfortable" as you say, then just keep doing those, and good for you!! If not, them try out some of the slightly more expensive things on the list.