As social animals, predictability in our primary relationships is essential. Loss of intimate connection is reliably related to loneliness, distress, anxiety, depression, guilt, shame, reduced self-esteem, and lower life-satisfaction. Romantic breakups may activate or exacerbate these symptoms. To underscore the depth of romantic breakups, musical lyrics are offered. Existential psychotherapy is specifically oriented toward experiences such as isolation, fears of the unknown, questions about lif3e meaning, and a balance between security and freedom needs. Existential psychotherapists primarily offer therapeutic intimacy and process empathy with clients in their here-and-now phenomenological worlds. Two foci of interventions are miscommunication and more complex structural readjustments. A client’s full experiential context is explored through three interlocking perspectives: human universals, cultural specifics, and individual subjective experience. The therapeutic context during romantic breakups includes clients’ culture of origin, and the contextual forces in the moment. A predictable sequence of relationship development and dissolution for individuals and couples in the process of breakups is offered, along with interventions at each escalation along with the somewhat non-linear process of post-breakup patterns of recovery. Considerations of romantic breakups within individualistic cultures are contrasted with those in collectivistic cultures, including those with arranged marriages, in first- and second-generation immigrants living in the United States. Unique, culturally-attuned therapeutic interventions are suggested.