People encounter video ads every day when they access online content. While ads can be annoying or greeted with resistance, they can also be seen as informative and enjoyable. We asked the question, what might make an ad more enjoyable? And, do people with different personality traits prefer to watch different ads - - could it be possible to better match ads and people? To answer these questions, we conducted an online study where we asked people to watch video ads of different emotional sentiments. We also measured their personality traits through an online survey. We found that the sentiment of people's preferred video ads varies significantly based on their personality traits. Additionally, we investigated when these ads are accompanied by content, how the emotional state induced by accompanying content affects people's ad preferences. We found that there was a complex relationship between people's emotional state induced by accompanying content and their ad preference when an ad highlighted either an alertness or calmness sentiment. However, when an ad highlighted activeness and amusement, the relationship was not significant. Overall, our results show that people's personality traits and their emotional states are two key elements that predict the tone of their preferred video ads.