What are your financial dealbreakers?

Since Valentine’s Day is approaching, I’m wondering what dealbreakers everyone has involving love and money. What financial red flags do you look out for in a partner?

I get tons of letters involving some very big dealbreakers. Some common ones include one person refusing to work (even though two incomes are needed), secret spending, gambling problems, and refusing to deal with mounting debt.

But here’s a letter I got last year where I actually don’t see any big dealbreakers, and I’m curious to hear what you all think: https://www.thepennyhoarder.co…-cant-afford-travel/

The letter writer is a widow who met a slightly older man. They’ve both raised families and share many of the same interests. She’s much better off financially than he is. He doesn’t have much money, but he also lives frugally.

The problem was that they wanted to travel, but he didn’t have the means to travel at the level she could afford. She didn’t want to travel on the cheap, but she didn’t want to pay his share. It didn’t sound like he was asking her for anything. He could afford his lifestyle just fine. He just couldn’t afford her lifestyle.

Having different budgets and lifestyles isn’t a red flag to me. It sounds like she really enjoys this gentleman’s company, so I think it’s worth trying to make this work, even if it means she has to pay more than half when they travel together. What do you think: Would you try to make this relationship work?

My big financial dealbreakers are refusing to talk about money and overspending to the point that you can’t make progress on your goals (like saving for retirement or paying off debt). What are your financial dealbreakers?


This letter was a conundrum to me when I read it last year, and still is.

My significant other likes to eat really nice food, i.e. nice steaks, does not eat fast food. and I am more of a budget eater when I need to be. He is debt free, and I am not and I earn less money than he does. I try to purchase what he likes when it is on sale, as he does the same for me; but sometimes I think I am holding my own debt pay off back a little by not being super frugal on the groceries, as I could be if I were just dealing with my own taste. I don’t have an answer so I am very interested in what people have to suggest. In my own opinion, there is more to split than just cost, there is effort, there is setting up adventures while traveling, hunting for good deals, so I guess I would take into account if a person was willing to do the reservation-making, deal hunting, packing/prepping, etc. that counts for something, too.


mine is worrying about the future i am 72 years old, had my job with the school for 20 years, about 12 years ago my husband said to me you don’t need a retirement , so i dropped out, now at 72 i am getting back into it, i do hope this can help me in some way, i am what my children call me a young 72 because i stay active, i will be able to buy back to the tier i was in by May 22 .


Hmm no dealbreakers for me per se, since love and money are compartmentalized into 2 different categories in my mind. One dealbreaker might be if the partner has the expectation that the person who is more well off should pay for everything – but that is less about money and more about an entitled attitude.

Re: above scenario. I think in the book I Will Teach You To Be Rich, the author talks about how he’s more well-off than his spouse and runs into the same issue. The thing that worked for him and his spouse is that the author, being more well-off, will pay for his proportion of things based on his income. For example, if he earned $500K/yr and his spouse earned $200K/yr, then his proportion is 5/7. So suppose they want to go on a nice vacation, do nice things. And suppose their trip cost $5K:

  • The author would pay about $3571 of it.

  • The spouse would pay about $1428 of it.

I think this is a nice compromise because it doesn’t restrict the breadwinner’s experiences while being able to travel with their loved one. And in addition, the non-breadwinner can still take financial responsibility for traveling (even if they are getting more value than what they’re putting in).

Whereas I think if the author had paid $5000 for the entire experience wouldn’t be fair. Unless the disparity between income is so huge that a proportional payment would always be close to 100% anyway.

But I guess that brings up 2 questions, which are:

1. What is the point of working very hard to earn a ton of money if you’re not going to liquidate it into good experiences with loved ones? Better to die slightly less rich with a loved one than optimally rich and lonely.

2. How much do you like the person? If you like them more than the extra money you can keep in your pocket, then keep them around. But if you don’t like them enough to have to spend extra money, then you don’t like them enough.

Tricky one, for sure.


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The only red flag I see in the letter writer’s example is her expectations of him. Though money going into our senior years is certainly important, so is good health, attitude and/or freedom to do what we’d like. If any of those assets are lost, those retirement dreams can evaporate in seconds.

My financial dealbreaker is irresponsibility with money. Living beyond one’s means. Doesn’t matter if a partner or family is wealthy or not, doesn’t matter the reason for the irresponsibility, it drives me crazy.


@omi That’s a great point about splitting more than just costs. Effort definitely matters!


Angie P has a point, and I will say my sister and brother-in-law did that style successfully, (ratio of incomes), for the several decades they have been married.


The letter writers situation sounds like mine! When I was dating, my boyfriend (now husband’s) income was 3X my income, and he was single and I was supporting 2 children. It was tough! He often paid for meals out for both and his part of vacations (and more) but I felt like I had to cover my own expenses. Really, coming up with 1000$ was MUCH harder for me- for him it was a day of overtime. I would save all year for something that he could just pull from his checking. Now we are married and he left his job and moved in with me. My income is 2X his. NOW he understands…

We work it out. Honestly, we don’t take expensive vacations, and live pretty simply. Its good!

Oh but I didn’t answer the initial question. My deal breakers would be: spending beyond your income, not having a good financial cushion, not planning for the future. I’m so very glad that we are on the same page financially!


Welfare It is true some people need the help and I hope they get it but, too many people consider it an early retirement plan. I see too much abuse of the system and have no desire to hook up with the abusers. Welfare should only be used by those who truly need it and only as long as they truly need it!

I appreciate this support we have about discussing love and money! Having dated both sides of the scale - one who had bad credit and owed me money, and one who was married to his money and belittled how much debt I had - there needs to be a partnership, balance and communication. I’ve learned that in a relationship, we both need to discuss finances, provide for each other and build wealth together because we love each other and want a life together.

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