People often value romantic relationships more than friendships, believing that the former bring greater psychological enhancement and well-being benefits. Some studies, however, have challenged this belief. Extending these studies, a secondary analysis was conducted using a four-wave longitudinal dataset that spans twenty-two years from adolescence to early midlife. Mixed effects modeling revealed that friendship involvement (i.e., being in close friendships) was associated with lower depressive symptoms. Findings regarding the association between romantic involvement (i.e., being in romantic relationships) and depressive symptoms were more nuanced. Associations were moderated by time: both involvements appeared to play more positive roles in adulthood than in adolescence, except for within-person increase in romantic involvement, which was consistently associated with increased depressive symptoms across the investigated life stages. This research confirms previous findings and extends former studies by distinguishing between- and within-person associations and extending the investigated life stages.