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I was planning to pair up two childhood friends, but upon aging up to teen, the boy found the girl very unattractive. She found him very attractive and would flirt with him, but he always rejected her. I tried changing his preferences to match hers, but for some reason, his opinion of her has not changed. Please help! This is ruining my storytelling!

What a twist on the story! He doesn't understand what he's missing out on.

Anyway, all you need to do is generate preferences for him, by going to Attractiveness -> Generate Specific and select Picked Sim Type in which you select her.

It worked! Thanks! :)