No, past the point where you don't care. If you continue for nine or ten more times, you start caring again. And it still doesn't work.
Before post edit: I see, you were talking about anxiety issues. I misunderstood the subject.
Not necessarily. Any attempt to actively and conciously avoid self-sabotage will result in self-sabotage. People (not just females) are surprisingly good at detecting hesistation. This is why it is better to act decisively
now than to hesitate over the perfect response. Yes, you'll probably screw up that way too, but it was an honest screwup rather than giving a self-serving impression, and therefore more survivable.
And it's actually less common to screw up this way than it is when you take time to consider, perhaps because this is not really a rational process.