: My boyfriend pays me $500 a month towards expenses. My mortgage is $2,200. He asked me to lend him $20K so he can build a business and retire in the Caribbean

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Dear Quentin,

I have lived with my boyfriend for the last six years, but we have been together for 10 years. We are already in our 40s, and have just learned to be happy in each other’s company. We get along well, and at this point we are both comfortable with the status quo — that is, we have no marriage plans in sight.

I pay $2,200 a month in mortgage and utilities, and he helps me out with $500 in cash and buys the groceries for our home. He was also able to take me to work, and saved me money on transportation. For the past year, I have been working from home, although I will probably be back at the office in September.

Sometimes, I wish he would contribute more to our expenses, but he doesn’t agree because the condo is in my name. I bought it before we moved in together and, although he lives here, he doesn’t feel it is entirely his place. I can’t stop wondering if I’m being unfair? Is he giving me enough support when it comes to our expenses? 

‘Sometimes, I wish he would contribute more to our expenses, but he doesn’t feel he has to since the condo is in my name.’

We don’t always see eye to eye when it comes to financial matters. Hence, we don’t consider marriage, and we are both protective of our respective assets. Ever since we met, he told me that he plans to retire to the Caribbean and how he will build a business over there that will allow him to retire comfortably in a tropical paradise. 

Well, he feels he is ready to start working on that dream now that he has saved enough money. I have never been thrilled about investing my money overseas, and although he has proposed I join him in that venture I have refused. Although I trust him, I’m afraid to lose money if something were to happen to him. 

After all, we are not even married, and therefore his immediate beneficiaries are his kids from his first marriage. He just asked me for a loan of $20,000 so he can have enough leverage without having to borrow from the bank. I don’t feel comfortable doing this without having some sort of guarantee or stake in the project.

‘He has never been particularly insistent that I become a co-owner, which strikes me as odd.’

I have been reluctant to join him in his venture and, yes, I have been reluctant to marry. He has never been particularly insistent that I become a co-owner, which strikes me as odd. Sure, I can join him in retirement, but it will be his property, which makes me think that is the reason he hasn’t seriously proposed marriage. 

I have a funny feeling that he is waiting to be the sole owner of his business, and only then propose marriage so if we get divorced, his property would not have to be divided as community property. And yet I also feel that I am not being supportive enough, and my decision might hurt our relationship. 

How should I approach his request without hurting him and our relationship? Twenty-thousand dollars is a lot of money even in New York, and I’m not rich. He did offer to pay $3,000 in interest when the time comes to pay it back, but I’m still not too fond of this idea.

So Many Doubts

Dear Doubts,

Do not lend him $20,000. You will likely never see that money again, even if you both signed a notarized loan agreement. His promise of a $3,000 interest repayment rings hollow, and it’s just one more sign of his false bravado and misplaced self-confidence. He is not ready to start working on his business.

Firstly, the only reason he believes he is ready is because he pays you a paltry amount of money towards living expenses. You pay a mortgage, utilities, property taxes, and in return he gives you $500, and saves you money on gasoline by driving you to work. Give this man a Nobel Peace Prize! 

Secondly, he is not ready to realize his dream if he has to borrow $20,000 from his girlfriend — the same woman who has made it possible for him to save this money in the first place because he is living in her home on the cheap. If gall was an Olympic Sport, he would get a gold medal!

‘His grand plans belie his ability to be financially independent.’

Thirdly, his grand plans belie his ability to be financially independent. If he does not feel like this condo is his home, he can buy his own home. He is moving to the Caribbean and will retire there after you have effectively helped pay his way for years? And do you want to move to the Caribbean? Has he even asked you? 

Here’s an imaginary letter to the Moneyist from someone who may sound eerily familiar: “How do I tell my girlfriend of 10 years that I only want to give her $500 toward her monthly expenses to live in her home, and borrow $20,000 so I can save for my future — without hurting her feelings?”

Let’s talk about your feelings instead of his feelings. Imagine this was your boyfriend’s proposal on your first dinner date: “I’ll contribute less than one quarter of your living expenses, and you give me a downpayment for my business so I can retire in the Caribbean. Waiter, I’ll have the steak. She’ll have the gazpacho!” 

Don’t wait for this freeloading fellow to propose marriage. Carefully consider that scenario. How would that improve your life? Maybe you are happy with the status quo, or maybe — just maybe — you’d be happier with a tenant paying $1,500 a week, and dating men who don’t treat their relationships like ATMs.

Also read: Jamie Dimon insists his workers return to the office — here’s why that’s a bit rich

You can email The Moneyist with any financial and ethical questions related to coronavirus at qfottrell@marketwatch.com, and follow Quentin Fottrell on Twitter.

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