Both everyday intuition and experimental evidence suggest that habits are difficult to change. However, despite the abundance of research, it is unknown whether the ease of habit breaking differs with respect to the most elementary forms of behavior, approach versus withdrawal. In the present study, we addressed this question by monitoring the formation and overriding of approach and withdrawal habits. In an initial habit-formation phase, participants intensely practiced approach or withdrawal behavior to neutral everyday objects (Experiments 1) and emotionally laden persons (Experiment 2) until strong behavioral habits were formed. In a subsequent habit-breaking phase, they were asked to change their behavior for half of the approach stimuli to withdrawal, and for half of the withdrawal stimuli to approach. Two intriguing results were observed. First, the results in the habit-formation phase showed that the typically observed speed advantage of approach over withdrawal cannot be diminished by practice. Second, the results in the habit-breaking phase showed that overriding a withdrawal habit by approach is easier than overriding an approach habit by withdrawal. In the latter case, participants were more often caught by their older habit, even when responses were bolstered by appropriate emotions. Thus, other than reflected in everyday thinking, approaching former enemies seems to be easier than withdrawing from former friends.