Why does the guy I like talk about his past crushes and first kissing experiences with me? Why does he call other girls cute and then grin at me?

Anonymous
He knows I have a crush on him. Lately he's been telling me about every girl he's ever kissed and how bad or awkward they were. He's also told me about past crushes and relationships and how his heart was broken.

He's called me pretty before and likes to play in my hair. He'll joke by saying stuff like "I like blue eyes. What color are your eyes?" He knows they're blue. We are always having extended intense eye contact. Then he says, "Ewwww", like he normally likes blue eyes but not if they're mine cause that'd be gross.

There's also a lot of poking my sides, bumping into me, playfully smacking me with pens, hitting my butt with stuff.
Is he trying to tell me something? He's 18 but is pretty immature.
Why does the guy I like talk about his past crushes and first kissing experiences with me? Why does he call other girls cute and then grin at me?
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