Although many studies of friendship support exist, little information is available on friendship's negative dimensions. Guided by a conceptual framework encompassing structure, process, and phase elements of friendship patterns, we explored troublesome aspects of friendship in a probability sample of community residents, focusing on four types of problematic friendships. Data from in-depth interviews reveal that problems with friends stem from structural features internal to the dyad, factors external to the dyad, changes in the extent to which lives intersect, and day-to-day interactions. These results are based on 42 respondents reporting friendship problems, usually with one of the four focal types of friends, about evenly divided across genders, but showing an age trend. Except for the ended friendships, some of which had dissolved long ago, problems were discussed in the context of ongoing relationships. Older adults do not necessarily terminate friendships that include certain difficulties.