The expectations of individuals involved in a relationship have long been regarded as important to the initiation and continuance of that relationship. This study examined the expectations regarding the benefits, time and money spent, and duration of the relationship between the volunteer and the single parent family involved in a Big Brother—Big Sister agency. The expectations of the volunteers, parents, and children of the 18 randomly chosen Big Brother—Big Sister matches were found to have an overall low level of agreement on the importance of the potential benefits of the agency. Significant differences were found between the intramatch expectations of matches where problems were reported when compared to those with no reported problems, but the expectations of the short versus long duration matches were not significantly different. These findings were discussed in terms of previous research on expectations as well as the orientation and initiation procedures of the agency. Further procedures were suggested to improve the congruency of expectations prior to the initiation of the match. Copyright © 1981 Wiley Periodicals, Inc., A Wiley Company