He isn’t very assertive....

I’m having trouble because this guy I’ve been talking to is a very sweet and awesome dude but....he isn’t very assertive? Like he’s not confident enough in himself to flirt with me or initiate a conversation or maybe when don’t talk for a minute hit me up and ask how I’m doing...it makes me feel like he isn’t interested or he doesn’t care. He comments on some of my pictures and that’s what usually starts a conversation between us but it’s never out of the blue like “hey just thinking about you” or what have you....
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Also Yesterday he was suppose to call me and we were texting before that and out of the blue he just says “okay talk to you later.” And I said “okay :)” and he just threw the peace sign at me and never called me....like wtf did I do?
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Not gonna lie that kinda hurt my feelings but it’s whatever. My sister says maybe he had something come up but don’t you think he could’ve at least communicated that to me? Like “hey sorry I’m gonna have to call you another night” or something just at least so I’m not over here thinking it’s my fault....
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The other day he was telling me about how Valentine’s Day sucked for him because he was alone so I flirtingly told him I wouldn’t mind being his valentine....just shit like that I’m always initiating and tbh it makes me feel so stupid after he pulls shit like this. Maybe I shouldn’t be assertive. Maybe I should just leave him alone. I’m more straightforward than he is and maybe that’s because he’s shy but I don’t wanna be making excuses for him. You either like me or you don’t. Maybe I should just fall back.