In recent years, research on high-risk athletes has focused mainly on personality traits, highlighting a complex and often ambivalent personality structure. Although scholars pointed out emotional difficulties amongst high-risk athletes, there exists to this day no in-depth investigation of the affective aspect. In an effort to address this so-far neglected question, this study offers the first thorough exploration of patterns of romantic relationships among high-risk athletes. Two groups were selected: people who practice extreme sports (N = 189; Extreme) and those who practice other types of sports (N = 207; Non-extreme). A series of tests were administered to evaluate romantic love, personality traits and self-esteem. Results showed that Extreme tend to display less intense feelings than their Non-extreme counterparts; conversely, their sentimental relationships are characterized by positive emotions and stable feelings, avoiding negative emotions. Hence, despite stereotypes which characterize Extreme as thrill-seekers prone to impulsivity, it seems that this group do not in fact seek as many thrills in their love life, but rather seek stability and contentment. Although still in it explorative phase, this study produced preliminary data which should be considered in devising further assessment and therapeutic strategies for this population of athletes.