This study presents an initial exploration and conceptualization of relational surprise experiences (RSEs) as communication phenomenon involving strategic relational maintenance behaviors with potential for positive and negative outcomes. University students in the Southeastern United States (N = 203) described a RSE that occurred with a close relational partner (romantic partner, friend, or family member), explained how deception was used to achieve the surprise, and reported relational benefits and drawbacks in an online survey. Seven types of RSEs were reported including gifts, events, visits, and destinations. Responses revealed that people considered surprises as relationally beneficial with minimal drawbacks. Although over one-third of the participants described their partner’s pants perceived the surprise as a violation of relational rules. Some participants reported both benefits and drawbacks to RSEs, thereby illuminating a nuance for traditional relational maintenance typologies. This study establishes a path to explore implications of RSEs for individual and relational satisfaction, happiness, and well-being.