Flynn should have seen it coming.
No, not the pan, you idiot! The pretty face and the hair and the attitude and the everything. That's what.
Flynn should not have been surprised with himself upon telling her his real name and his less than princely history.
However, the surprise over her MAGIC HAIR! is justified, but he is a man of many talents, so he could mask it. You would never have known about his surprise.
Flynn should have realized sooner that he was falling for Rapunzel - but no, it took some old crazy bat and the two Stabbington's jumping him and tieing him to a boat with the crown for him to realize it.
No, it took the two Stabbington's jumping him and tieing him to a boat with the crown and sending him to his doom, without knowing what had happened to Rapunzel, for him to get it. He's pathetic.
Flynn should have recognized it for what it was - but no, somewhere between the Snuggly Duckling's tunnels and showing her the lanterns, he became oblivious.
And, well, he wasn't sure of when it happened, but when he woke up in a boat, being accosted!, he wanted to protect Rapunzel, and maybe get his hands on the frying pan again.
His arrest wasn't supposed to be until the next day, after the lanterns, after... he's not sure what would have come of him giving her her dream. He likes to think it would involve 100% less clothing, but he was almost positive it wouldn't happen like that.
Now they don't even have the chance.
He's got less than that time to do anything, really. There's not even time for a daring Flynn Ryder escape, with head bashing and nut busting.
He can't focus, anyway. Maybe it's that the Stabbington's probably have Rapunzel, or, if they don't, she's with the old bat who he'd love to be in the same room with, as long as she's tied up and he's got the pan. Maybe it's because he has no idea what's happened to Maximus and Pascal - not that he cares about them. Rapunzel does, so he has to keep them around, and safe.
Flyn should not be surprised. He shouldn't be surprised with anything, except he is, because when did he do anything to deserve Rapunzel? He'd been a theif for years; he'd tried desperately to get her out of the deal; he'd taken her to the Snuggly Duckling, just to scare her. And yet... she seemed to lie him enough to trust him with the crown.
There was a sinking suspicion that the crown is her crown, that she is the lost princess - and that makes his wonderments ever more frequent. What would a princess - the princess ever want with him?
As he sits in that cell - and oh my god, what is that smell?! - Flynn realizes that he shouldn't have been surprised that his heart was pounding out of his chest whenever he was in Rapunzel's presence.
Well. It's too late, now.