Guy's Behavior

Is this guy I like shy, not interested or confused?

I’ve known this guy for years, recently we’ve met up twice and he’s really sweet, he did us a picnic the first time. However, I’ve always been the first person to initiate conversation and ask to meet. When we do meet, it’s really nice. He’s called me pretty, cute and has asked about my past relationships. I don’t get the vibes that he doesn’t like me at all but I’m not sure, I just think he would be more open in talking to me. He has initiated in the past but nowhere near as much any more. We do talk occasionally when I talk to him first, and he still calls me cute names like “babe” or “dear” (maybe because he’s being nice?). He likes to continue the conversations though. Anyway... my question is, do you think it’s worth me initiating things all the time? And how do you think I can start a next conversation? He has said he’s really shy before, but I don’t want to waste my time. It makes the most sense to straight up ask him but I wanted to get you guys’ opinions.
Is this guy I like shy, not interested or confused?
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