I have a tie for two things…
- I took off with window open
- During a cross-country I forgot to tune to local airport and was making calls all the way to landing on wrong channel.
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It wasn’t me, but I had a funny experience with a friend of mine who had recently earned his PPL. We were flying cross country and out of nowhere, nerves got the best of him on the radio, and he asked for clearance to an airport to the southwest, but said his intention was to fly east which he doubled down on after ATC tried to clarify. I could hear the ATC’s brain short circuit a bit as he tried understanding what we were doing until my buddy realized his mistake.
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Not my mistake (I’m not a RL pilot), but a while ago I came across this video:
And I think it’s great that he admits his mistake and even shares it publicly so everybody can learn from it. 
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Well, other than the “trusting the PIC and flying too close to severe weather” story I mentioned in the other “scariest thing” thread…
One thing I can remember is during training, taking off on a solo night cross-country and immediately hearing a fast, continuous whap-whap-whap sound on the side of the fuselage. Instantly realized the tensioner strap of the seatbelt (thankfully not the buckle) was caught in the door and hanging outside in the airstream. Sheepishly asked tower for a lap in the pattern with a stop and go, and cracked the door and pulled it in at that point. No real problem, just remember to always fly the plane.
Once, as a 42-hour, freshly-minted private pilot, I almost departed with the pitot cover on. Long story, but let’s say that was due to rushing, expectation bias, and negative transfer in a different, fairly new-to-me aircraft outside of the recently completed (initial) training environment. Fortunately I realized it before we even taxied out, but that was a little walk of shame and I haven’t taken the pitot inspection for granted ever since.
Other than that, I can find little things every single flight that I could have done better. These days it’s usually a radio call that I could have trimmed up, or maybe I could have been a little tighter to standards in a maneuver. I haven’t gotten complacent, but age and family have caused me to be a lot more aware and cautious.
I was lined up in the check-in lineup and saw a girl in front of me (I was a lot younger then). “She’s cute”, I thought to myself. Get on the plane and guess who’s sitting beside me? We got along great and had a fun conversation. I even ended up riding into town with her in the airport shuttle van. I said bye without getting her number. She seemed taken aback as I left. Dumb.
Not on a flight but stationary on the ground.
I remember reading a story (probably on Quora?) about a pilot who was discussing landing gear lever operation with his junior first officer, and wanted to show the latter that pulling the lever up while on the ground would have no consequences and the gears wouldn’t be raised. Can’t remember what type of aircraft it was, certainly not GA, definitely not an airliner but still something of substantial size.
The pilot pulled the lever and the aircraft was written off… Apparently there wasn’t a squat switch or it didn’t work or whatever.
I did just that, pulled the gear switch up while sitting on the ground and doing run-up. To this day I am not sure why… I was setting up everything for the takeoff and THIS is one of the things that I “decided” to do. 
Fortunately the squat switch worked 
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Not adhering to the important phrase aviate, navigate , communicate and actually doing communicate (with my wife, then new girlfriend) navigate, aviate. Touched down in a multi engine piper at VRef + way tooooo much, oscillated down the entire runway in front of many spectators before doing a go around (luckily with both props and nose gear attached) . My wife has never flown GA since and I am still reminded of my landing ballet performance on a regular basis !!
Lesson learned and always followed since, aviate first !.