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I really do want to keep a good conversation going but I never know what to say, and sometimes i struggle with finding something to reply with besides okay
Why not try something original?
Like if someone say to you "I'm fine too, thanks", instead of saying ok, you can say: "Hello Fine. I'm dad." Or "You are fine? I thought you were *insert name*".
Be creative. Just put the first non offensive and funny thing that pops in your mind.
Or if it's too hard for you because you are not a creative person, take a random word on a random page of a book and make a challenge to include this word in your next message.
Some people these days make it hard not to reply with just okay because they're antisocial or simply are talking to you rather than with you they want to rant but don't want to hear about you