Gambles that involve a large but unlikely gain coupled with a small but likely loss-like a lottery ticket-are known as positively-skewed. There is evidence that people tend to prefer these positively skewed choices, leading to what is called a positive-skew bias. In this study, we attempt to better understand under what conditions people are more drawn toward positively skewed, relative to symmetric, gambles. Based on the animal literature, there is reason to believe that preference for skewed gambles is dependent on the strength of the skew, with a greater preference for more strongly skewed options. In two online studies (Study 1: N = 209; Study 2: N = 210), healthy participants across the lifespan (ages 22-85) made a series of choices between a positively skewed risky gamble and either a certain outcome (Study 1) or risky symmetric gamble (Study 2). Logistic regression analyses revealed that people were more likely to choose moderately- and strongly skewed gambles over certain outcomes, with the exception of when there were large potential losses (Study 1). However, a stronger skewness did not increase preference for positively skewed gambles over symmetric gambles, findings which also may depend on the valence of the expected outcome (Study 2). Taken together, these results suggest that there may be a greater preference for more strongly positively skewed gambles but it 1) is dependent on what other gamble is presented and 2) is most prevalent for positive expected values. Additionally, contrary to previous findings, we did not find strong evidence of an age-related increase in positive skew bias in either study. However, exploratory analyses revealed that decision making strategy and cognitive abilities may play a role.