I would suspect that he's very perceptive and in not a very nice way. And you are very perceptive, but you're ignoring it, which is what he wants you to do.
He has perceived that you don't think you're much of a catch, so he knows that lots of flattery will get him places (in your pants, in your purse etc)
You have perceived, with your gut, that he's a bad boy, but because he's acting nice, you're allowing him to manipulate you out of that feeling.
Healthy relationships don't start with one person doing little but tell the other repeatedly how lucky they feel to be... well, you can't even say 'in a relationship'.
Healthy relationships don't start with one person being freaked out by the other in any way at all.
If you're freaked out, that's a red flag. Predators look for people who ignore their red flags. Trust your emotional response here, and always. If you're freaked out, it's because he's being weird. If he's putting you off, it's because he's not doing things in the way you like.
'I'm freaked out... but is it just me..?' YES, it's just you. But that seems, for many, to mean that it's something they should disregard. 'Oh, it's just me and my silly old emotions.' But your emotions are all you have. If you are happy, nothing else matters. If you are sad, nothing else matters. Your emotional responses are vital. It is just you. Pure you. Unfettered, unadulterated, unusual, one-in-a-million you. And that you is giving you messages. Listen to them. That you will show you the way to happiness and healthy relationships, if you choose to listen to her. She's the real you, who has been silenced whilst your other relationships fell to bits. She needs to be heard and validated.