OK, then here’s one more opinion/take…
I’m going to skip the relationship advice, there’s a whole industry and many resources devoted to that…
First off talk to your friends and seek advice, they know you and your situation much better than any strangers on the internet.
You mentioned in your first post that you liked your job, is it currently a career or just something to pay the rent? In other words, do you have a lot of experience in your field and is that important? The reason I ask is because if you’re looking for an airline career you’re looking at probably two years and at least $70K of debt plus whatever your living expenses are before you will be in a position to be hired. During that time you won’t have much of an income. If you’re currently established in a career, how much money are you giving up? If things don’t work out with flying, would you be able to resume your old career? In other words, what’s the opportunity cost?
Money aside, you will have to put your life on hold for two years. Unless you have a large sum of money saved up that precludes buying a house and starting a family. After a couple of years and once you get that airline job you won’t be around a lot, is your fiancé OK with being more or less a single Mom? Keep in mind that there is no guarantee you’re going to get that dream job and fly at a major air carrier. You may end up at a regional carrier and make a comfortable living, which is great and arguably better if you really like flying. Unless you are one for the few that just LOVE aviation and can’t get enough of it, after a year, maybe two, it will be just another job. And of course there is always the possibility of another economic recession and the inevitable furlough. Back to the old job…
OK, that about covers the doom and gloom. As you probably know, in the current environment, your chances of landing an aviation career are the best they have been in a generation. I wish I was 10 years younger because it would be very tempting… If I was 34 and single I’m pretty sure I would pull the trigger and take a run at it! The airline industry is all about seniority so the longer you wait the less opportunity you will have for the best schedule, most money and adventure. In other words the best lifestyle.
That said, I don’t see how it can be done after getting married unless your fiancé is willing to put the house and kids on hold for at least three years while supporting you in your endeavor…
You have many decisions to make that honestly you should have made a long time ago. Whatever you do, it would be worth getting a First Class medical or at least getting a consult from an AME just to make sure you’re not about to disrupt your life only to find out your aviation career is over before it even starts.
Good Luck with it!