Personal freedom has known to be positively associated with well‐being. As socioeconomic conditions advanced in modern societies, the pursuit of personal freedom has also gradually increased. This trend further coincides with the decline in marriage and fertility rates. This implies that the pursuit of personal freedom could be related to lower involvement with the family. The current study examined how personal freedom would be related to family compositions and well‐being across different socioeconomic conditions using a large‐scale data set. The results indicated that personal freedom was the most consistent predictor of well‐being. Marriage‐like relationships were also positively related to well‐being. However, the relationship between the number of children and well‐being was mostly insignificant except for the most recent data showing a positive relationship. Results also indicated that personal freedom did not lead to singlehood but was negatively related to the number of children. Socioeconomic conditions of countries and different time periods moderated these relationships. The influences of different socioeconomic conditions and the time period were discussed further in the paper.