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I can't raise the Everett affection points at all. I've tried sitting with him at lunch, working with him and using cheat codes. Is there anything I can do to raise it so I can go on more dates with him?

At a certain point you can't get closer to someone as just a casual dating partner, you have to ask the guy to be your official boyfriend. It's possible you're at max affection for a non-committed relationship and that's why it's not going higher. Try calling Everett up on the weekend and looking for a button of two people in the bottom right corner of the date selecting screen. If that's there, click it to get the option of having Everett as your boyfriend. Let me know if that works out for you!

It worked! Thanks for the help :)

Great! I'm glad that helped.