I have a pretty Type A personality, so by the time I went out to find my first cache, I had spent a couple weeks researching the hobby and already knew a fair bit about the ins and outs. I went with my brother (his first time, too), and we went 8 for 9, I think.
Any way, our first cache is still one of my favorites. It was a warm day in late winter, so there was little underbrush and almost no bugs. We had a nice, short hike along the top of a bluff in the woods, with some of the best views of the lake around here. It took about 5-10 minutes of searching to find the ammo box in plain sight. We hadn't brought any swag with us, but when my brother saw the foreign coins, he left several Subway coupons from his wallet, and he was pretty excited when another cacher logged shortly thereafter how excited s/he was to find the coupons.
I think we may have to revisit that cache again soon. Maybe in honor of our 100th find.