Young novice drivers are more prone than older drivers to get involved in a risky driving situation. Some young drivers underestimate risk while overestimating their driving abilities, increasing the likelihood of engaging in risky behaviour. Age and inexperience both influence risk estimation, though it is not clear which of these variables is more important. Can drivers’ willingness to engage in risky behaviour be assessed in a similar way to hazard perception skill using video-based risky situations? The aim of the current study was to assess whether a video-based tool could measure the willingness to participate in risky driving situations and whether it can distinguish between different types of risky driving scenarios across gender and driver age groups. We also explored the moderating effect of age and gender on drivers’ experience in relation to the risky manoeuvres and participants’ willingness to engage in risky situations. Participants were presented with naturalistic videos from the perspective of the driver that contained active risky situations (result of driver’s own actions) and were asked to make a decision regarding a potential action (to overtake a bus/bicycle or pass through an amber light) and whether they would accelerate at this point. Participants reported that they were more willing to accelerate and overtake cyclists and buses and less willing to pass a light in amber. Young drivers were more willing to both engage in the risky behaviours and accelerate than older drivers, with young males reporting higher scores than the other groups. Gender differences were observed, with males being more prone to overtake and pass through a light in amber than females; however, this difference was not observed for the intention to accelerate. All the above effects remained when we tested the impact of experience on decision making while controlling for age and gender, although driving experience was no longer significant. These results demonstrate that drivers’ intention to assume risk can indeed be measured in a similar video-based methodology to that used by hazard perception tests. The findings raise the possibility of assessing and training drivers on a wider range of safety-related behaviours.