She clearly wasn’t too excited about going on the date in the first place...saying, “yeah, I guess” and her telling him straight up that he’s not even her type to begin with was a major red flag. Then constantly asking for reassuring: are you sure?? Are you sure?? Yeah?? Yeah?? If someone isn’t all that excited to go on a date with you and telling you that they’re not sure if they really want this is a clear indicator that they’re just not that into you...idk how it could be anymore clear. Him going on that date was probably a free meal for her or even if she didn’t pay, he was just someone to hang out with cause she was bored or felt so sorry for him, that she went on a pity date. The fact that she didn’t even try to hide how unenthusiastic she was about the date THROUGH TEXT and OP STILL attempted to pursue her because he really likes her, you just lose a little respect for a guy like that.