So, I've been with my BF for 5 months. Over this time, I have observed that we have very different approaches to spending.

I am quite frugal. I only make about 68k a year but have amassed about $100k in savings by age 35 that I intend to use towards a down payment on a house someday. I don't have any debt. Not even a car payment. I paid for my last car in cash. I pride myself in being debt free.

My boyfrind makes about $175k a year take home. He grew up poor, and has a strong "you only live once" mentality and has spent most of his bachelor years going on expensive trips, vacations, and music festivals. He also eats out and door dashes on a regular basis.

I don't know his exact financial situation, but he has indicated that he currently has about 20k in loans that he is paying off. He told me it happened because he overspent on vacations expecting his normal annual bonus (which is usually around 20k) which didn't come through due to unexpected financial strain at his company. He keeps a personal budget. He refers to his budget frequently, but then still spends a large amount on entertainment expenses.

What I don't know is his total net worth and if it is in the negative or positive. If he has a high interest bearing savings account or CD with a rate of return higher than the interest rate on the loan, then I wouldn't be that concerned. But, it honestly concerns me that he even has debt at all at his income level. Just the thought of debt makes me squirm. My worry is that if we get married, I will be constantly worried about living paycheck to paycheck due to his entertainment spending.

At the same time, I've been allowing him to treat me. He told me up front that he likes to take care of his partner and likes to cover the majority of expenses. When I tried splitting costs more evenly early in the relationship, he kept saying, "please let me treat you. Contribute what you can afford, but let me take care of you." I obliged and have been getting showered with trips, concerts, festivals, lavish dinners, etc. I feel guilty about this though since he has debt.

He has admitted to me that he needs to slow down his spending and that his long term goal is to buy a house. (We live in a super expensive area where starter homes jump off at $1 mil, we would need to pull together at least $200k for a down payment to avoid PMI). He recently said he wants to shift his focus to building a life together and slow down on the trips in particular. He also just got his own apartment after having lived with roommates his whole adult life, and it is much more comfortable for him to do his own cooking rather than door dash on a near daily basis.

He's been talking a lot more recently about wanting to spend his life with me and hinting at getting engaged. Before this happens, I want to ensure we are on the same page about our financial future. I want to be an active participant in our combined budget should we get married, and I would like to get a prenup as well. At the same time, I don't want to "mommy" him and tell him how he should be spending his money.

How would you approach a serious money conversation with him? I know these are potential red flags, but he's got a lot of green ones as well. He is still progressing in his career and has is eye on moving up to the executive level in the tech/startup industry. I have trust in him that he can continue to progress and get the spending under control, but I honestly have lingering fears (i'm a worrier).