Guys are supposed to be the pursuers, does that mean I’m supposed to initiate conversations with women most of the time even if we’ve already talked?

guys are supposed to initiate the first conversation it seems like but do I initiate the conversations after that? At what point am I just bothering them and at what point and I’m still pursuing them?
Guys are supposed to be the pursuers, does that mean I’m supposed to initiate conversations with women most of the time even if we’ve already talked?
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