There is robust support for the notion that playfulness is important for how people initiate and engage in their romantic relationships. Our study sought to extend the knowledge on associations between four facets of playfulness (Other-directed, Lighthearted, Intellectual, and Whimsical; OLIW) with facets of relationship satisfaction (RS) in 116 middle-to-older age couples (median = 54 and 57 years in women and men). In comparison to younger samples, we found lower expressions in Other-directed playfulness. Using Actor-Partner Interdependence Modelling, we found that (a) older couples showed comparatively higher similarity in the single OLIW facets and their profiles than previously found in younger couples; (b) similarity is again unrelated to RS; and (c) findings on playfulness-RS associations partially replicated, with Other-directed and Whimsical playfulness showing the numerically strongest actor and partner effects, but mainly in women. We discuss the differences in similarity with regard to an attrition effect. Overall, we conclude that playfulness is important in older couples in similar ways as in younger couples.