This study explores gender differences in older widowed persons' interest in dating and remarriage, and the implications of these desires for psychological adjustment to loss. Analyses are based on the Changing Lives of Older Couples study (N = 210). Men's interest in dating and remarriage is conditional upon the amount of social support received from friends. Six months after spousal loss, only those men with low or average levels of social support from friends are more likely than women to report interest in remarrying someday. Similar patterns emerge for interest in dating 18 months after loss. Persons who both want and have a romantic relationship report significantly fewer depressive symptoms 18 months after loss, yet this relationship is attributable to their greater socio-economic resources.