Although a majority of studies show that acting in a more extraverted way is beneficial for one’s well-being, there are also indications that acting counterdispositionally is emotionally draining. In the current study, we try to explain these discrepancies by comparing indirect measures of counterdispositional extraversion (one relative to the trait level and one relative to the average state level) and we introduce a novel direct measure that taps into perceived counterdispositional extraversion. By using Multilevel Polynomial Regression and Response Surface Analysis in a large ESM dataset ( N = 187 individuals and N = 17,547 repeated observations), we found that for both direct and indirect measures of counterdispositional extraversion, higher state levels of extraversion related to higher levels of positive affect (PA), and this effect appears to be stronger for individuals high on average state and trait extraversion. Findings for negative affect (NA) were less consistent, with perceived deviations from one’s typical behavior relating to higher levels of NA. Altogether, our findings show that acting in a more extraverted way is better for increasing PA, on the understanding that subjective experiences of atypical behavior can be experienced as harmful.