Music streaming companies collectively serve billions of songs per day. Radio-based music services may intersperse audio advertisements among the songs as a means to generate revenue, much like traditional FM radio. Regardless of the monetization approach, the recommender system should decide when to play content that the listener is known to enjoy (exploit) and content that is novel to the listener (explore). Recommender systems that rely on this explore/exploit type framework have been deployed in a wide variety of applications such as movies, books, music, shopping and more. In this work, we investigate the impact of different ad/song sequences on listener behavior. In particular, we focus on the impact of exploring new song content for the listener given the previous sequence of ads and songs in the listener's session. Our results show that the prior sequence matters when considering song exploration and that this prior sequence has an impact on the listener's tendency to interrupt their current session.