Backpacking is obviously quite fun, and that's a big part of why I do it - enjoyment. But when it gets super hot and humid, or cold and wet, or windy and rainy, or whatever, one can begin to ask themselves why they do it (see the WHY? thread in Philosophy & Technique).
It's usually more fun to go backpacking when it's perfect out, and when everything goes right. When you loose tent stakes, gear malfunctions, your lighter runs out of fuel, or anything else goes wrong, it could be easy to let it ruin the trip. On the other hand, it can also be a great opportunity to learn or practice new skills, and still have fun. You'd be surprised how what appears to be a crappy situation can actually end up being a great memory.
It's easy not to think of snakes, dry creeks, faulty gear, lost tent stakes, cuts, blisters, etc when we idealize in our head how a trip will be. So one question you should ask yourself is do you love backpacking and what comes with it, or do you live the idea of backpacking... they are two different things. If you really love backpacking, then pick a perfect weekend and head out. If your not sure, do the same thing. A nice weekend with good conditions will brighten your spirit and remind you why you enjoyed it in the first place.
In the past, I've normally been a fair weather camper. Hey, I do this for recreation, right? If I was headed out for a weekend trip and it was forecasted to be rain all weekend, I just did something else. I've changed my mentality on this recently, and will now head out unless conditions would actually be dangerous. Well see how this goes for me as time goes on, but I also don't need help getting motivated to do it. I love it. Which is why I say, pick a perfect weekend, and go have fun.