What does it mean when a guy asks if you've ever had a boyfriend?

my coworker that I've been hanging out with, randomly asked me last night if I've ever had a boyfriend and I said a few times and then he started talking about how he's never been in one and that he just hooks up with people because he was self conscious and what not. And then he went on about how he thinks I'm smart and like innocent but I know what's up or something I don't know. He's always saying how awesome I am, does it all mean anything?
What does it mean when a guy asks if you've ever had a boyfriend?
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