The new president of Nigeria, President Muhammad Buhari, sends out mixed messages in his mandate to the Nigerian military force to defeat Boko Haram within the next three months (October– November 2015) as well as expressing willingness to negotiate with Boko Haram for the release of the remaining 219 schoolgirls under Boko Haram’s captivity. Following a recent field research in the northeast Nigerian states of Yobe and Bauchi, and interviews conducted in Lagos, Anambra, Kaduna and Abuja, this paper considers the prospect of dialoguing and negotiating with Boko Haram. The paper concludes that Boko Haram’s unrealistic goal of Islamising the secular Nigerian state should not dissuade the government from engaging the sect. Also, the remaining 219 girls represent to Boko Haram bargaining chips for any negotiation with the government. The paper also concludes that the Nigerian Government should aim at inducing moderation and flexibility in Boko Haram’s demand by compelling the group to submit its objectives to public judgment through the existing political system, as well as carrying out a careful study of the group’s sphere of influence (internal cohesion, sponsors and external connections) to better understand ‘who’ to engage with, ‘when’ and ‘how’ to engage with the sect.