Stay alert, get to know him better, try different situations, see how he behaves towards others - waiters, children etc. how does he talk about women? As individuals, objects, types? Is he open and allowing time to gain your trust and get to know him, not hiding things?
I'm 42 and would find the paying for everything odd, more a my parents' generation idea, I'd be expecting to go halves or take turns after the first date. Not necessarily any harm in it but possibly indicative of an 'ownership' idea, possibly not. Would he be offended if you booked something for you both? Is there a financial disparity between you that he's happy to smooth over and just wants to be able to do nice things at this stage, rather than getting bogged down in practicalities?
Yes there are nice single men in their 40s. People who aren't fussed about 'settling down' and having children younger just don't have the drive to, well, settle, that many others do.
My own thoughts in any similar situation would be, is he a player who's a bit too good at the dating game, empathising, winning your confidence? No harm if you're playing the same game. Is he a sentimental fool with a romantic notion of how you are and a relationship might be? Lack of insight makes them hard work later and likely to drop you when they find you're not their princess. Is he lacking awareness of his own problems or behaviour, someone who's made the same mistakes a few times and still doesn't quite get it? If he ever talks about his exes, ask about their pov, how did he think it was for them, what did they say were the reasons. You might be able to deduce more from that than he has.