I don’t think there’s kiruv daas when there’s no possibility of communicating personally, or knowing the other person’s identity. Even the gemaras case of m’achurei hageder is different because the man knew which woman it was.
Also most don’t shmooze about personal things. Not the ideal, but honestly I’m here because i like writing and expressing the perspective of the yeshiva world, which is lacking here and online in general.