Jan 12, 2016. Juuuuuust in case there were any question marks about messaging while online dating, know this: you should send the first message. Yes, YOU. Once they’ve responded, what next?. Find a friend who is also online dating;. Not in the second message, but usually somewhere around second or third. They found that mentioning guacamole when you’re online dating will massively improve the number of inbound messages you receive….