Theoretical models of complicated grief (CG) suggest that maladaptive motivational tendencies (e.g., perseverative proximity-seeking of the deceased; excessive avoidance of reminders) interfere with a person's ability to recover from their loved one's death. Due in part to conflicting evidence, little mechanistic understanding of how these behaviors develop in grief exists. We sought to (1) identify behavioral differences between CG and non-CG groups based on approach/avoidance bias for grief-, deceased-, and social-related stimuli, and (2) test the role of the neuropeptide oxytocin in shaping approach/avoidance bias. Widowed older adults with (n = 17) and without (n = 22) CG completed an approach/avoidance task measuring implicit bias for both personalized and non-specific grief-related stimuli (among other stimuli). In a double-blinded, randomized, counterbalanced design, each participant attended both an intranasal oxytocin session and a placebo session. Aims were to (1) identify differential effects of CG and stimulus type on implicit approach/avoidance bias [placebo session], and (2) investigate interactive effects of CG, stimulus type, and oxytocin vs. placebo on approach/avoidance bias [both sessions]. In the placebo session, participants in the non-CG group demonstrated an approach bias across all stimuli. Intranasal oxytocin had an overall slowing effect on the CG group's response times. Further, oxytocin decreased avoidance bias in response to photos of the deceased spouse in the CG group only. Findings support the hypothesis that oxytocin has a differential effect on motivational tendency in CG compared to non-CG, strengthening evidence for its role in CG. Findings also emphasize the need to consider differences in personalized vs. generic stimuli when designing grief-relevant tasks.