Objective The focus of this study was on the impact of spousal loss on the development of chronic pain thereafter. More specifically, the aim was to investigate the effect of experiencing low preparedness before a wife's death and the widower's chronic pain 4–5 years after loss. Methods In a population‐based study in the years 2004‐2005, anonymous questionnaires were sent out to 907 men in Sweden who had lost a wife to cancer in 2000 and 2001. The questionnaires contained questions on the man's preparedness for his wife's death and his physical and psychological health at follow‐up. Results Altogether, 691 out of 907 questionnaires were retrieved (76%). Younger widowers (38‐61 years old) with a low degree of preparedness for their wife's death had an increased risk of experiencing symptoms of chronic pain (odds ratio 6.67; 2.49‐17.82) 4‐5 years after loss. The same results did not apply for older widowers (62‐80 years old) (odds ratio 0.81; 0.32‐2.05). Widowers who experienced chronic pain were at an increased risk for psychological morbidity, depression (relative risk [RR] 2.21; 1.31‐3.74), anxiety (RR 2.11; 1.33‐3.37), and sleep disorders (RR 2.19; 1.30‐3.69). Conclusion Our data suggest that low preparedness for a wife's death may increase risk of chronic pain among younger widowers 4‐5 years after loss. In addition, we found comorbidity between psychological symptoms and chronic pain among widowers. These findings call for studies on possible mechanisms in the association between low preparedness and morbidity and on how to increase preparedness for a wife's death to cancer. Copyright © 2013 John Wiley & Sons, Ltd.