That's actually a tough question that you ask. I understand that it's a scary time for you but maybe that means that you aren't ready for marriage. Part of committing yourself to a woman is being willing to love that woman no matter what: "In sickness and in health..." Do I think it's be a double whammy to bring up a prenup? If it were me, yeah. I'd be very hurt and very scared that the person I was about to committ my life to was already thinking about what to do when it falls apart. Obviously you don't want it to fall apart but thinking about this sort of thing already could be an indication that you don't think it will work out. The best suggestion I can make is to find a place to do pre-marital counseling. Now, with that said, let me tell you the kind of place you need to go to. Your average run-of-the-mill pre-marital counseling will be a couple hours long and you'll have to sit there and listen to someone. That's not for you (or for anyone in my opinion). The kind of pre-marital counseling that really works is one where you have to come prepared. A long list of questions of "How would you respond if...", "What do you think about..." and other scenarios should be answered ahead of the the appointment for discussion during the appointment. Pre-marital counseling if fabulous time to find out what your future wife really thinks about situations that are very difficult or uncomfortable to bring up in conversation. All topics should also be brought up: finances, kids, sex, who's in charge of what chores etc...You should leave your appointment feeling two things: that you know your fiancee better and life is going to be ok with her. If you don't feel that way after the appointment you need to talk to her about either going to pre-marital counseling somewhere else or you need to talk about your relationship and your future together. One other tip I want to give you is in regards to filling out the questions. If you find that you're tempted to lie to make yourself look better, don't. It's imperative that you both answer with 100% honesty - let your flaws show! It's scary to let your flaws show (especially the ones that you think you've kept covered) but I guarantee if your fiancee doesn't already know about them she will soon. It's imperative that you answer this way as the alternative is to have the truth come out after you're married and have your fiancee wondering why in the world you changed. I could go on and on but I've already typed out enough advice. Think about what I've said and let me know if I can be of further help.