The "Plenty of Fish in the Sea" achievement.

In Shadow Complex, a shameless ripoff of Super Metroid in its game mechanics, you play a guy who drives a girl out to a remote location in the Pacific Northwest and she gets kidnapped by a military organisation. You're cut off from your vehicle, but fairly early on in the game you are able to return to the start point. You are able to get in the car and drive away and an achievement pops saying "Plenty of Fish in the Sea." So you win but your guy gives up on his girl, leaving her to her fate.

Hack/NetHack had a similar thing where you could just leave without completing the main objective (retrieve the Amulet of Yendor, which has a random chance of appearing at the 35th level and below, and make it back out with the Amulet). I remember it saying something snarky on the Amiga version, but I don't recall exactly what. Like it said you went on to live a boring life or something like that. Any time you felt like you were locked out of the objective or outnumbered by enemies without the means to fight through them, you could backtrack and leave (though, things like disease, hunger, and thirst could take you before you got out) and you'd "win" (as in, you get to keep living).

I enjoyed Wolfenstein 3D's quitting messages, "Chickening out already?" or "Press N for more carnage. Press Y to be a weenie." and the like.

The old point-n-click flash game Johnny Rocketfingers had a bunch. There was a part where you had to find a way out of a jail cell or something, and if you used the hand tool on a crack in the wall, your character just says "feels cracktacular."

Oh, and there was the old original You Don't Know Jack game where if you told the host "fuck you" or something similar in the answer box, they'd just lose patience with you and exit the game for you.

There is no game

I like the simple messages you get in Quantum Conundrum every time you die. They're not super serious things, but just things that the main character will never get to experience as they grow older, ranging from mundane things like not getting a drivers license to more realistic teen/immature young adult fantasy of eating a whole can of whipped cream as a meal.

Crosscode has a ton of dialogue changed if you turn on NG+ modifiers, such as carrying over levels or using a "cheat code" for ludicrous damage, 1shotting almost everything.

One NPC quotes the "you cheated not the game, but yourself" copypasta.

The Soul Urn in Deadlock is very chatty and will constantly sass you while you're trying to pick it up for your team.

I was beginning to feel abandoned.

You do know where you're supposed to take me, right?

You're dropping me?!

In Sam & Max Hit the Road, when you repeatedly try to pick a stationary object up. https://www.youtube.com/shorts/szTtHNEg6vo

Having to grovel to lower the difficulty in God Hand.

What is this game called? 👀