Yes, that one time I sold many of my N64 games for a PS2. I wholeheartedly regret it and decided then to not sale my games again.

I do not sell or trade my games...I have however lost much of my older games in a bad break up years ago. The most notable of those games are...

Ogre Battle SNES
Tactics Ogre PSX
Ogre Battle 64
Chrono Trigger SNES
Chrono Cross PSX
Ocarina of Time N64
Majora's Mask N64
A Link to the Past SNES

These games seem to sting the most, even after replacing some of them...

Yeah, that was one I kept as well. I liked Major'a Mask too much to sell that. Perhaps some day you can still get back your N64.

Super Smash Bros 64 and Donkey Kong 64 for 27 dollars cash.

I needed food

I own maybe 30 physical games right now. I've probably owned 400 over the years. So, that's quite a few sales. I've never felt bad about a single one. I've managed to make gaming a low cost hobby, and reselling games is just the way it has to be in order to do that.

With that said, I wish I held on to Final Fantasy 15 and Recore, as both have DLC that I would like to play. I just sold Farcry 5, and I'm a little concerned that I'm going to wish I hadn't when some DLC comes along. I think that's about it though.

Smash Brothers Melee

Mario Party 2

Goldeneye

Bubble Bobble 2 (mostly because I ended up pawning it for like 90 bucks when it's now going for roughly 400).

I’ve thrown out consoles and all the games I’ve owned (Atari 7800, Intellevision, Vic 20, SNES, N64, PS1/2), but I’ve never sold one. I’ve mostly done it in a move and I didn’t feel like lugging them around. I gave a car away too to a landlord for the same reason. I’ve repurchased an Atari 7800 because I missed it so much, but the others - to hell with em.

But lately I’ve been collecting for my older systems. If I come across an Xbox, GameCube, or Ngage game I don’t have, I usually buy it if it’s decently priced. I must say though, I do miss Stunt Race FX for the SNES.

Mario Party 6 and 7.

I forget why I did it but not having these 2 games really hurts my soul. Hours of fun and i've been craving another go at them.

what hurt me the most, were when i sold xenogears for psone, miss you😞

One day I sold so many N64 and Gamecube games, but I can't remember what for. Nowadays I try to rebuy them one buy one if I see them. Years later I realised that this was extremely stupid and I will never do that again, even if it is a game that I have mixed feelings to. For exmple, there are three Wii U games that don't satisfy me as much as all the others, which are Nintendo Land, Legend of Kay: Anniversary and Scribblenauts Unlimited. Still, I won't sell any of them, because I know that one day I will feel an urge to take quick look into them once again.

The games that still hurt me to not possess are Baten Kaitos, Skies of Arcadia Legends, Star Fox Adventures, Second Sight, Super Smash Bros. 64, Super Smash Bros. Melee, Banjo-Kazooie, Banjo-Tooie, Mario Kart 64, Super Mario 64 and F-Zero X.