Host plants possibly represent the strongest selection pressure for the evolution of reproductive traits in phytophagous insects. In a first part of this chapter, we review how plant quality affects both female and male life history traits and their respective reproductive success, and how the production and transfer to females of male sperm and associated nongametic substances (spermatophores as nuptial gifts) also depend on the host plant choice. At first glance, it seems that reproductive traits in phytophagous insects should be selected to maximize the success of this short-term interaction between host plant and phytophagous insects. This, however, ignores the fact that variation in reproductive success is detrimental to long-term fitness, which may explain that reproductive traits depart from their short-term expectation in unpredictable environments. Bet-hedging strategies – as exemplified by spatial or temporal dispersal (e.g., prolonged diapause) – can therefore evolve in such environments, as described in the second part of this chapter. The knowledge reviewed in this chapter is also integrated in the broader applied perspective of insect pest population management.