1. The first time flying (disco flight). I’ve always been a bit afraid of heights, and really didn’t know how things would go. I was a bit stressed taxiing out to the runway, and then the instructor had me add power for takeoff, the wheels lifted, and I didn’t worry about that any more.

2. First first solo – At the same place, I soloed in a 172. Unfortunately due to job changes and moves I had to get out of flying for about 5 years and never flew after that.

3. Second “first” solo – It took a bit longer to get to solo this time, but those three trips around the pattern in the Alarus were quite memorable.

4. First flight after checkride – Like you, I took my wife for her first small airplane ride. It was a great feeling taking a non-DPE passenger for the first time, and even more so with it being my wife.

5. First x-ctry with my wife – Going to visit my parents and taking dad for a quick trip over his house was very nice.

Even leaving it at 5 leaves off some pretty memorable moments, IMO.

@Mark: correct, top three positive moments. I admire your capacity to decide stop flying. As you might know, I’m in a temporary stop after our family move to Germany. I do plan the re-start of my flying carefully, with a focus on being sufficiently trained. Not only fun flying, but good recurrent training. I hope you’ll be able to do so someday…

The other kind deserves mention, assuming you survive them. I won’t name three, but one would be realizing that you’re in a situation that will rapidly take you beyond your training. That’s what made me quit flying, not from fear but from knowing I didn’t have the time or money to train to that level.

Second best moment so far was my first flight with a passenger, after I finished the GFPT, which in Australia allows a student pilot to take passengers to the training area and back. This was a colleague of mine, his first time in a light aircraft, and he thoroughly enjoyed the experience. The responsibility of being PIC with a passenger on board changes a lot of things, I think I was a lot more cautious than on my own, checking everything twice, making lots of radio calls for arranging separation, keeping my eyes out of the cockpit most of the time, etc.

Best moment so far was my first solo nav exercise. Everything went just fine, I found the remote airstrip where I was supposed to land, landed there, had lunch, chatted with local pilots, went back, all without a glitch. Very very satisfying experience. I couldn’t stop smiling to myself while cruising at 6500ft on my own away from the home base.

Hopefully I’ll manage to bump one of these three ‘best moments so far’ off the list in a couple of month when I take my PPL checkride. In which way it will become a memorable moment still remains to be seen