It's been a while since I've played this, but from what I remember, you need to plan things out pretty carefully. The game IS the thing that this ending is talking about, so you're on the right track there. Play the game every time you get the opportunity (so every other day) to make sure you complete it. And fulfill Eli's requests each time.
I don't quite remember how I fulfilled the other conditions, but I think I just did things to annoy Eli (like going to work and choosing dialogue options that lower their affection) to make the world red. The only thing you should be doing to raise their affection until the world turns red is playing the game. And then, once the world is red (which might take a while), start doing everything you can to raise their affection. Finishing the video game was the hardest part for me, because it makes it take longer to piss them off.
I think the steps are the same for the "went outside" ending, except you go on a date (to the same location every time I think) instead of playing the game. So you would go to the park, for example, every other day while doing everything else to annoy them. And then you'd raise their affection when the world turns red.
Let me know if this works! If it doesn't, I'll try playing the game again to figure out what I did to get those endings, lol.