It’s when me and my boyfriend finally met irl ( we were dating online)
So we went at his place to play WoW, and we were doing War Campaign on my Warlock, and saw that awesome Sylvanas vs Saurfang cinematic.
So I guess BFA? 
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My warlock friend who i know from cata times joined my 2x2 push in bfa s1 end when i have just returned to the game and together we unlocked the awesome lion dread glad shoulders for me.
I was standing with his ally toon void elfie and dancing at one of the boralus harbour 
For the alLIONs!
For me, it was Wrath, mate 
In fact, I came back FOR BFA, thinking it would be going back to the old days.
To be fair, I have to wonder if my cynicism now is born out of understanding, peering through the veil of game design. Of course, retention systems existed in Wrath, but they weren’t visible to me.
Now, the day new content drops, I immediately know all strats needed to beat it. In Wrath, I didn’t know how to beat all content. I learned with the game… but the info was there, I just didn’t know the channels to gain it.
I have fond memories of so many games I beat without spoilers, without engaging in the game’s community, and discovering everything for myself. Bought Sekiro on day 1, without knowing exactly what it is. Turns out it is one of my favorite games.
To be fair, back in Wrath the game was designed to be an RPG, and systems more or less fed into the fantasy. Now, the game is just a random mashup of systems that do not serve to enforce any fantasy. It’s just… a skinner box.
My best memories of this game? Well, my first was when I was levelling as a tank in Scholomance dungeon? and was just acting as a 4th DPS- a guy whispered me and guided me through the tanking process which was decent of him. But I just loved MoP for its overall design, gameplay and class design
Back during tol barad days (when we still had mass summon as a guild perk)
I remember that we had taken 2 bases, then i did the mass summon the whole team to the 3rd base and we won instantly, so full team on same base capped the flag in a few seconds.
Dono if that’s the “Best” But it’s for sure one of the most Vivid.
I will do one for each expo I played.
Vanilla: Easily this would be me and my brothers (we all player together then) engaging in world PvP in places like burning steppes or other likely high level zones where you’d start feuds with other players. Great fun. Also heading into places like Ashenvale for the first time was epic.
TBC: as a new draenei player reaching the Exodar, the music, it was huge, everything about that starting experience was “stranger in a strange land”. Also crossing dark portal for first time…having played WC2 setting foot in outland was freaking epic
Wrath: Played WC3 TFT so not gonna lie just heading to Northrend for first time was pretty cool. Particularly when I first went into Azjol Nerub. Big highlight for me this expo was leading my first raids when doing Naxx, Ulduar and ToC.
Cata: Mostly rolling my first cow Pala (had same name as this guy) and focused PvP and I was a royal pain in BGs as a healer and I loved it. Paladin In cata was awesome.
Hiatus
Return in legion, for me highlight memories here: the good is definitely me being able to play a demon Hunter from WC3 and explore a new class, that starting experience was epic. The bad is worth mention: Argus. Just wth. I have loved draenei since TBC and expansion of eredar lore, and honestly Argus and especially Mac’Aree was just a huge dump on my expectations after seeing draenei stuff when levelling in WoD content.
BFA: Operation Mechagon with community 110% what great days those were when it was new. The first hard mode runs…haha.
I’ve a couple.
One I can think of is back when i first started this game in July 2016…
I made a Worgen Druid, and I played her through Gilneas, loving every second of it… then I reached Darnassus, my god was Darnassus amazing, the music, the colours, all of it was just… lovely and serene.
And I remember, I then went to the Jewelcrafting trainer to learn the profession, because this was when I was really new, and I though rings and necklaces had models! So I figured “hey, I’m gonna make all this lovely jewelry in this game so if any of my friends join I’ll be able to give it to them!”
How little I knew of how the game worked… oh how little I knew.
I like this memory just because it really reminds me of what it was like when I started this game, when everything was new, and I was but a small babe wandering in this behemoth of a game, unsure of what anything was.
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I have 2 thats stand out, once was during cataclysm when i firs started playing in 2011 questing through wetlands on my tauren pala ( later switched to draenei ) and was in the middle of looting a herb when deathwing flew over and 1 shot me. Id never experienced any thing like that actually made the world feel alive.
2nd memory was actually during warlords of draenor camping the rare spawn riverbeast in talador for the mount, with a raid group of 30 ppl everyone just talking and fishing and goofing around, a lot of my best memories from wod were actually raiding and camping rare spawns.
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I haven’t played that long…
Defeating Alleria Windrunner to get the 5 Mask solo FoS. I was so close to rage-quitting WoW thanks to Visions, but I persisted, gearing up through Visions and Warmode Conquest points over many weeks, and finally killed her with just a tiny amount of sanity left when I’d told myself “this time or that’s it”. The one achievement in WoW that I’m proud of (I don’t do M+ or raid).
Finding my way through that maze for the Lucid Nightmare mount. So much relief!
Not a specific memory, just a general collection of BfA Warmode memories. The endless battles, the random solo fights, dodging the rabid packs of roflstomp-addicted Horde gankers… Was all so much fun, I really miss it.
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That maze was a nightmare for me I actually mapped it out in ms paint
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Wandering around leveling my first character in Dun Morogh during BfA not able to grasp how big the world really was. Since only New Tinkertown was like New Tinkertown, the leveling experience went downhill from there. 
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Legion was my first official expansion (not counting wotlk, mop, cata, wod private servers), and I loved it, pvp was great, gear sets were amazing, artifact weapons were awesome, mage tower, area music, stuff to do, I still miss legion, I often go there and fly to some areas. Expansion felt complete, and then we got bfa fiasco, and now SL, which is ok in pve but pvp is pure trash, its like p2w, I dont have that feeling like in legion, like buying new car and cant get enough of it. Did I said I miss legion ? Yea…
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I started in Cata, and almost everything up to level 40 was AMAZING! I could pick many moments from that, but I’m going with the day I got flying as a level 60.
Ahhh.
Lifting off, seeing the roofs of Stormwind from the air for the first time - I didn’t know they were colour coded to their zones - and then doing a tour of all the zones I had levelled through, taking a final revenge on all the mobs that had beaten me along the way. And all the time careful where I was flying, in case I damaged my gryphon’s wings in the trees.
There was much else that was great from 60 to 85 and the end of the expansion, and through Mists. And then Timeless Isle - the greatest patch zone ever added!
Timeless Isle was the last great memory I had in WoW.
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Well… it has to be the time i told my other half how i felt. I was in a quarry zone in Icecrown, Wrath.
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I have two big fondest memories of WoW - my first was when I first tried the game in MoP through a friend, and was just so taken in by it. I’ve loved Warcraft lore since I was a kid thanks to the original Warcraft games, and I was obsessed with Chinese culture at the time and Pandaria was - and tbh, still is - the best fantasy country I’ve ever seen in any form of media. It’s beautiful and every aspect of it captures my imagination. I used to go there just to afk. I made a female Tauren Monk. I was really bad at the class but I loved it so much. The class captured me as much as the rest of the game did. I remember getting whispers like “A girl Tauren monk???” Like people had never seen them before. I can’t remember how old I was but it was a long time ago, I’m nearly 25 now and I know I was definitely a teen. Every limited play session I had made me fall more in love with the game I’d wanted to play since I was basically a child.
When I finally got a properly stable income two years ago, one of the first things I did was buy a WoW sub. That was my second happiest memory. I made that girl Tauren Monk. Still main her, through thick and thin, through all of WW’s ups and downs. She now has a sister, a Warrior, too!
I’ve had plenty happy memories in-game too - it wasn’t all first-time experiences - but there’s too many to properly remember. One I remember fondly though is after about a year of farming Invincible, I finally dropped him myself. It was the week before the SL prepatch dropped, so a good few months back. I’d been totally enamoured with him (my friend had him and let me see him) since my brief trial in MoP. He’s been my ride ever since.
Edit: I should mention I also played on an MoP private server for a bit, but my time there was eh so I didn’t think to mention it. I still consider retail to be the first time I properly tried WoW!
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Stranglethorn vale for me holds so much memories!
While most view it as a war zone, I viewed it as a great place for adventure and even a romantic walk or swim. My character was dating this Troll lady and it was her idea to go to Stranglethorn. It was so romantic and beautiful… apart from being chased by tigers to death. Once we got to that romantic waterfall/beach area in Stranglethorn we had a picnic and just stayed there chatting. Then we went to booty Bay. This was back in Cata I believe
Too bad I can’t remember where that romantic place is today.
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First time I got gladiator in TBC. I knew it was a possibility, but you didn’t know for sure back then before you’d see the mount in your mailbox. I logged in that morning and found my season 1 drake, I was over the moon. 
Sure there were. I had tons of fun killing Garrosh in MoP while being the solo healer, for example. I had tons of fun playing arenas with my mates in Warlords. But the highs of later expansions still didn’t quite rate as high as TBC for me.
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My first 1v1 as a rogue in Stranglethorn Vale in patch 2.4.3 (i lost) when i started to love pvp. Or my first 2k reached in 2s in Retri/Restosham comp 3.3.5 patch. I truly miss 2.0-4.3 when wow was more like RPG than E-sport Game.
Oh and killing Murlocs in Silverpine forest as my first ever made orc warrior when i grinded from lvl 1 to 15 because i didnt know about quests 
And my guild mate told me about Quest Helper addon so i made new character Tauren Shaman just to abandon it at lvl 20 because i thought its pure healer class so then i switched to rogue and leveled to ~40 but i’ve switched to paladin at the end of bc because rogue was too hardcore for me. Good times.
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Standing over the body of the Lich King as we all celebrated the mount we had collected, 25 man meta Icebound Vanquisher.
It was also a sad moment for me, unknown at the time, as it was to be the last raid achievement my guild and I would run as raid leader before the GM decided to go super hardcore and bring in a load of hardcore raiders who then destroyed what was up to then a very laid back, very sociable and at our own pace guild. Fair enough the ICC 25 man mount run wasn’t current, but it wasn’t a cakewalk either.
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Finally being able to afford a (secondhand) computer that could run WoW, during TBC.
Honourable Mentions:
Getting my first mount at Level 30.
Getting Flying at Level 70.
Completing the Rep grind for the Winterspring Frostsabre.
The Headless Horseman’s Mount dropping.
Finally getting enough gold to buy the Grand Expedition Yak (in WoD).
WotLK
MoP
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