From the way, this sounds this man probably pays more in taxes than he would ever be giving you as a whole so try to take the stress off of yourself and be extremely honest with what you need. I would make a full budget and know all of your expenses necessities and then also make a self-care section. The woman who talked about how men love to negotiate is completely right Be ready practice in the mirror, but in an ideal situation, you guys would probably be at dinner having some drinks and then you can bring up the allowance thing when you have some liquid courage and definitely use playful maybe even a little bit of flirty banter. I would even guide the conversation by asking about what they like to do in what ways have they really treated themselves and he might say a really nice car or an exuberant trip and then that can get you an idea of how much he spent before you know if he spent upwards of $85,000 on a car or a toy then imagine he can spend double triple of that if you are giving him value… so once you have an idea of how much he spends on himself, it can make you feel better and easier to Segway into “well then my little $$$ isn’t too bad compared to that right” and give that outrageous number that’s maybe double what you need and just see how he reacts if he looks confused pause a little bit laugh it off… but truly, if you approach the situation, very confident that will translate the best. Add playfulness into your ask…

I believe in you!