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Is it always my job to send the first message(of a new conversation)?

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SW-User
If they aren't doing it then yes. If you want to get to know them, that is. Otherwise just don't care about it.
SW-User
@SW-User I mean, I tend to be the first one most of the time. After I start the fourth/fifth conversation... that has to tell me that they’re not interested, right?
SW-User
@SW-User you mean with the same person?
SW-User
@SW-User With the same person yes. I guess my question sucked.

My whole point is; if I’m forced to be the one to initiate the conversation everyday, that must mean that they’re not interested in talking to me right?

Yet, I’m a bad friend if I don’t initiate it.
SW-User
@SW-User ah... Well. Depends if you notice they aren't interested in talking to you, if the conversation becomes boring, then no need to contact them again ...

You may wait some days to contact them again if the conversation seemed OK.

With most people I talk are like that. But our conversations are always interesting. Or must of the time. Hahaha And yes most of the time I contact them.
There's only one person that contacts me everyday. And I reply to him when I can or want.

So depends.