EDIT: Holy moly this actually got huge. If you just want to know the history of my current nickname, it's the paragraph that starts with "Lastly, around 3 years ago".
I'll join in.
Using a nickname I liked was always a struggle for me.
At first I just used my first or first and last name together (I used to hang around on NetBattle under the name Afonso, which is my first name, for instance, when I was like 11 or 12 years old).
After some time, I decided to actually invent a nickname. I was terrible at coming up with names. So I stopped using my first name and invented the nickname sakagashiko (terrible nickname and no one is allowed to be ashamed of their nicknames after this lol). Stopped using it some time after.
After some time the Lockerz site popped up. I liked the name so I started going with lockerz96, being 96 my birth year. I still used it in my Skype account until fairly recently, when I created a new one. Skype was the last place I still used that name. I stopped using it because it felt too generic and not very smart to just use a website as nickname and slap my birth year.
At the same time I decided to check Pokemon simulators again (PO at the time), after watching some videos of BW (I really disliked DPP back then, so I took a hiatus while the 4th gen was around). I decided to try a Baton Pass team, which was a complete joke, having no competitive experience. After a couple of battles a random guy started spectating all the matches I entered and I eventually inquired him about it. He said I was a really good player and was trying to learn from me or something of the sort. He was obviously making fun of me, which got 14 or 15 yo me, who was already going through depression, get really obsessively affected about that. My love for Pokémon* wouldn't let me quit, even with my morale on all-time lows, so I went with the nickname "Noobish Noob" on PO and later on PS!, so that if I ever played terribly people wouldn't judge me as much, because, you know, I was a noob. Ironically, I actually was on the top 10 of BW UU PS ladder back when that was the most recent gen for a lot of time, using a team built around Yanmega, a Pokémon no one used in UU. I only used this name in Pokémon Sims.
After that, in an online game I used to play, there was a guy whose nickname was TheDoomBug. I really liked the sound of it. Also I like bugs. So, I started using TheFlamingBug. It also sounded good and I was into Yu-Gi-Oh! at that time, so I'd just slap a
Warm Worm as avatar and be done with it. I still use this nickname on Steam. However, I never really liked it, it never felt original and unique.
Lastly, around 3 years ago, my best friend's little brother (who, despite being 6 years younger than me, became one of the closest friends I've ever had), who is also a diehard fan of Pokémon, was discussing Pokémon with me. Eventually the subject of me never really liking one of my nicknames popped up. I decided to merge his favourite Pokémon (SCEPTile) and mine (HeracROSS) and thus Sceptross was born. That was the first nickname I used that I really enjoyed. I still use it, have no plans of changing it and the only regret I have about it is not capitalizing the first letter. I think non capitalized names look bad. Maybe I should actually talk to Lutra about that
Fun fact: Every time I changed my nickname, someone told me they actually enjoyed the former nickname. That's something I actually find amusing.
*Seriously, I easily have dozens of thousands of hours dedicated to the Pokemon franchise, I have no words to describe how much it has impacted my life.