From the beginning I'd planned to XP WHM, because I wanted to be the kind of person who could help everyone and be looked up to for always doing so (ha! ha! WHM respect. =P) When I first started, I was lost in town for ten minutes. Then I ran outside on my WHM and died to a Savannah Rarab. Had no idea how the enemy con system worked, and for a while didn't even know if "decent challenge" or "even match" was tougher.
When I was talking to Klank while he was XPing on Goblins, I imagined green guys with knives and swords. I also thought Windurst Woods was a forest or something (clearly wasn't paying attention to zone names)
I subbed THF til 30, as it was the only other job I had levelled. I unlocked SMN, levelled that a bit, and subbed that until I hit 75 - I thought it was better than /BLM because of Max MP Boost, and only much much later did I learn that Max MP Boost was +10mp, not +10%, and that you get virtually the exact same amount of MP as you would from /BLM.
I spent a lot of my time camping Spipi while levelling jobs from 7-12 or so via murdering EPs (also thought 12k for a stack of silk thread was totally awesome...though I NPCed the first stack and asked Klank why I only got like 7k for them when I heard that they were 12k/stack - I hadn't even figured out how the AH worked at that time...). To this day I'm something like 15/71 Spipi.
I remember being scared to death of Yagudo Initiates and their ability to hit me for 10 damage twice. I ran far, far away whenever I saw Yagudo because I swore they aggroed from a mile away. I remember newbies having to zone Yagudo and they'd sit there at the zone until some "high level" wandered by and killed it for us.
I remember seeing a Mithra in Opaline, I thought the armor was beautiful. I checked the AH: 200k per piece? I'd never be able to afford that. And only two have ever sold in Windurst. It must be really rare...
I remember getting randomly traded a pearl to an LS called "Perfekt". I unfortunately remember no one from it except Anklebiter, though I believe I met Sindern in that shell, who was my first ingame friend and wound up helping me with a good deal of things...
Made a lot of friends along the way, more than I can name off the top of my head...but I digress, what I've said thus far hasn't really helped anyone in a way. Times I enjoyed most? Probably camping Acha d'Armas with Lanien, helping a few random shells do HKTK/BQ, claiming Padfoot with Lavi, killing big NMs with TheFlock (though unfortunately I don't get to do that much anymore, Bune was an especially nice memory). Also enjoy lending a hand to Pasquale, he's a real fun guy. Pulling people together and convincing friends not to give up on our Dobsonfly attempts (think it took us four runs to get Stouter both the ring and Sallet due to new recruits getting their stuff and splitting, but we got em!)
List could go on forever, really...