Motivated by results about “untangling” closed curves on hyperbolic surfaces, Gupta and Kapovich introduced the primitivity and simplicity index functions for finitely generated free groups, dprim(g;FN) and dsimp(g;FN), where 1≠g∈FN, and obtained some upper and lower bounds for these functions. In this paper, we study the behavior of the sequence dprim(anbn;F(a,b)) as n→∞. Answering a question from [17], we prove that this sequence is unbounded and that for ni=lcm(1,2,…,i), we have |dprim(anibni;F(a,b))−log(ni)|=o(log(ni)). By contrast, we show that for all n≥2, one has dsimp(anbn;F(a,b))=2. In addition to topological and group-theoretic arguments, number-theoretic considerations, particularly the use of asymptotic properties of the second Chebyshev function, turn out to play a key role in the proofs.