@socprof
I was taught that the best use of pepper spray is when you aren't being held securely yet... you spray as close to their face as possible then get the hell out of there.

Weapons, even pepper spray, need a little training to do properly.

Same with kicking a guy where it hurts. Guys have an instinct to protect that body part, so you really are unlikely to connect. Better to make the threat (my boot, your balls), then if he actually attacks, go for his eyes or throat.