[NEEDS INPUT] Incredibly friendly trait makes possibility challenge impossible

I had this 'issue' too, but it turns out you need to do the interactions with 'acquaintances'.  Incredibly friendly makes the sims 'friends' really quickly so it won't count.  It's an issue with tier 2 of the challenge as the 'good deeds' can be done with/for everyone on tier 3 and tier 4 (I found this out in my Positivity Challenge' Let's Play. My work around was to form or join a club (if you have Get Together) as it's a way to meet sims without introducing yourself so you start out as acquaintances.  You could also try talking to work colleagues as the same should hold true (if your sim has a job).

Best regards,
Jennifer