Carnival was my first thought! I think she could take him there when they are bffs. Until then... hrm, Selphie can either show him how to play guitar or something, or she could show him the chocobos and he can go for a ride? Crafts are good too, but Selphie kinda sucks at them.
I can toss up a log for them sometime this weekend if you want...or maybe you should because I'm not sure how I'd set up how she's persuading him to it...
Hrm...I could chuck up a general one of Selphie playing her guitar someplace again, and he could stumble across her. She's pretty good at forcing people into fun! ^^
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Yeah, he'd freak out at the carnival for reasons beyond just not liking to have fun, so that might not be that enjoyable...
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Oh no! That sounds scary - but maybe eventually she could try to persuade him otherwise. Or help fix him up when he freaks out.
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