Our experiment investigates whether children handle recursive possessives (R-Poss) in a more adult-like manner than recursive relative gradable adjectives (R-RGA). While the abstract notion of indirect recursion underlies both categories, we ask whether individual syntactic-semantic properties determine different acquisition paths in English for R-Poss and R-RGA at the 2-Level (the deer’s friend’s mushrooms, small big mushrooms) and at the 3-Level (the deer’s friend’s sister’s mushrooms, small small big mushrooms). The results indicate that older children perform better than younger children on 2- and 3-Level R-Poss. However, this trend is not observed for R-RGA where both age groups perform similarly, successfully handling 2- but not 3-Level R-RGA. Analysis of individual results reveal that children who are successful with comprehension and production at 3-Level R-RGA are also successful with 3-Level R-Poss, but not the other way around. We conclude that 3-Level R-RGA is more challenging than 3-Level R-Poss, arguing that this difficulty arises from R-RGA syntax-semantics which involves a set-subset relation and gradability relative to comparative scales.