Decide what you want. 😉 Do you want to get married? Live together? Date from different homes? Are you looking for someone who’s financially compatible enough to travel and enjoy entertainment that requires a particular budget? And if so, is that a deal breaker for you? (It sounds like it might be, but you haven’t spent enough time deciding the answer.) If you want to remarry, there are some obvious issues here and possible deal breakers. If you want to date, then you can do so — but he won’t be able to travel as you will. If you want to play the field a little longer and see if there’s anyone out there who’s better matched to you, then you should do so. Since I don’t hear a ticking clock in your questions, take your time and figure out what you want, and when you do, if he fits the bill. Just because he’s in love with you doesn’t mean you’re a match. And just because you’re incompatible for marriage doesn’t mean you can’t see each other monthly while you play the field.