This paper explores predictors of outgroup partner “fit” (the degree to which an individual is seen as representative of a group), and whether fit defines generalization from a discrete intergroup communication experience to intentions for future contact with the outgroup. In an experiment, 288 undergraduate students imagined a conversation with an older target who was presented either positively or negatively. The positively valenced older adult was seen as being more representative of older people in general (high fit), and this link was stronger for those with more past positive and fewer past negative communication experiences. Fit mitigated the effects of imagined interaction valence on intentions for future intergroup contact. A positive older partner perceived as fitting the category “older people” resulted in greater intention to communicate with older people in the future than a negative partner; individuals who saw their partner as atypical showed the reverse pattern—they were less likely to report intentions for future intergenerational contact after a positive than a negative manipulated interaction. The findings show that negative intergroup communication can, at times, have positive effects, and positive contact can have negative effects.