The widely accepted liberal paradigm that people are born free and the empirical fact that sometimes we feel or do have obligations to various groups we are members of rest quite uneasily together. The joint commitment that we may have in the latter case is the basis on which Margaret Gilbert develops quite plausible theory for legitimation of political obligations. However in her account the individual freedom seems forgone. In this paper I show this and several related problems of the actual contract theory and discuss a possible way to avoid them. I suggest that obligations to the group may be understood to arise not from mere belonging but from the actual participation in certain collective activities coupled with the ordinary meaning of that participation within the group. This solves the problem but only at the expense of considerably atenuation of the meaning of freedom. That is why I find my solution not entirely satisfactory and maintain that the actual contract theory remains at odds with freedom.