This qualitative interview study examines challenges college students may experience in extracurricular dialogues on contested sociopolitical issues. It also discusses approaches that students claim support them through the challenges of contested issues dialogues. This study found that college students encountered challenges including difficulty expressing disagreement, tensions related to their identities and group representation, and difficulty building trust and openness with peers in dialogue. Despite these difficulties, students also developed skills and capacities to bridge differences, to build community within dialogue, as well as to learn about themselves, others and sociopolitical issues. Through participants' accounts on how they perceive and negotiate these challenges, the study is intended to portray in-depth student perspectives about this critical aspect of peer dialogues on sociopolitical issues. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]