I've never really played with Charisma in all my Simming years. So, last night, I decided to give it a shot.
My sim was happily building her skill, using a little influence from TestingCheats to get her friends. After completing her second skill challenge, I noticed one that should've been fufilled isn't. It is the challenge to know 20 Sims - albeit having around 30 Best Friends, the counter remains firmly stuck at a measly 4.
The only explanation I can offer is this - she met 4 sims online, and the rest were met with cheats - does this not register because she hasn't physically met them?