Gettyimages.com/Friends hanging out at a club paying for something

If you’re in a relationship with someone for a long time—especially if you live together—then money is bound to swap hands back and forth. Just look at the Venmo history between a couple. They probably send cash to each other for falafel, movie tickets, Uber rides, concert tickets, and plane tickets all of the time. And, let’s be honest: nobody is really keeping perfect score of who owes whom what in committed relationships. There are probably some beers I never paid my boyfriend back for and some packs of gum he never got me back for. But when you get to that level of comfort financially, you may reach a new level of money talk: your partner asking to borrow money from you. I mean real money like in the hundreds and thousands figures. So, do you go there? It’s not an easy question and the answer is also not easy. Here is when you should and shouldn’t lend your man money.

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For basic bills: It depends

If your serious boyfriend of multiple years needs money to cover basic bills while he’s out of the job, you should probably be able to lend him that. The caveat would be if he weren’t actively looking for more work. But if he’s aggressively pursuing jobs and just not getting one, and needs help paying his car payment for a month or two, that’s a worthy thing to chip in for.

For a (well-planned) dream: Do

Sometimes you’re fortunate enough to have a little nest egg, or a very high-paying job, while your partner isn’t quite as lucky. If he’s pursuing something and he could use a little capital to do it—maybe to, say, build his website for his business or film a short that he’s submitting to festivals—it may not hurt to help him out. The important thing is that he has thought this through, has a plan, has clear objectives, and has realistic ways of reaching those objectives. But if he has a business plan, and you have the capital, help him out.

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For investment, with collateral: Do

If you’re in a serious relationship, some investment opportunities may come your way that your partner cannot afford on his own. If he could, for example, loan someone money for their home mortgage and get a 12 percent interest rate (a deal that came across my desk recently), that’s a great investment. Why? Because if the borrower defaults on payments, the lender gets their home. It’s basically a win-win. If your partner has a chance like this but needs help making up the principal, maybe you should participate.

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To patronize his art: Hold off

Here’s the thing: your partner can get a day job just like every other artist has to while he pursues a singing/acting/comedy/writing career. Heck, you probably have some passion projects of your own but you aren’t counting on someone else to fund them. You have a job to fund your dreams—not someone else’s. No matter how talented of an artist he may be, he isn’t above working for a paycheck until his paintings start making money.

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To lend to someone else: Hold off

Don’t get involved in lending your partner money so that he can lend it to someone else. It’s too tricky. He may feel for a relative who needs money but, you should only lend money to someone with whom you have a close enough relationship to communicate openly, and pursue your payments/interest. Don’t lend to a third party.

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When he has a spending problem: Hold off

If your partner needs money because he spent money irresponsibly in the first place, well, sadly, he’ll just have to feel the burn and learn his lesson. You should never, ever lend money to someone who has a proven track record of mishandling money.

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To go to school: Do

If your partner wants to go back to school and has a realistic idea of what he’d like to do with his degree, you can help him out. You’re really just investing in the future of your relationship if that degree can help him earn more.

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To pay off student debt: It depends

A lot of people fall victim to crippling student loan debt. If you and your partner need good enough credit, together, to…buy a home…and that can only happen if someone pays off most or all of his student debt ASAP, you may consider helping him out. The question is, however, is he behind on payments? If so, why? Is it due to irresponsible spending? Well then you may want to rethink joining your finances with this person.

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In a new relationship: Never

Do not lend large sums of money to someone you’ve only been dating for a few months. Honestly—and I know it sounds strict—you probably shouldn’t lend someone more than a couple hundred dollars if you’ve been together for under two years. Let that honeymoon delusion wear off before making financial decisions.

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Without conditions: Never

It doesn’t matter how long you’ve been together or how much you trust each other: you are entitled to conditions when you’re handing over your hard-earned money. Don’t be afraid to write up a contract and have your partner sign it. If he respects you, he’ll sign it.

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If he’s ever lied to you: Hold off

If someone is capable of lying to you about one thing, he’s probably capable to lying to you about a lot of things (like what he’s doing with the money you’re lending him). There should be complete trust in a relationship before money starts exchanging hands.

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As an investor for his business: It depends

If your partner has an incredible idea for a business, he has done his research, and he has the systems in place to launch it, you could be an investor. But, if you don’t believe in your partner’s business idea, you don’t need to risk your money to spare his feelings. Remember, money is money—it isn’t personal. You are never obligated to hand over your money.

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For medical bills: It depends

You probably should only help a long-term boyfriend with medical bills. Again, this would be a boyfriend of two or more years. If you break up, you may never see that money again.

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To collection agencies to go away: It depends

This, again, could have to do with your joint credit scores and your financial goals as a pair. You may need to help your partner pay off some debts to make the collection agencies stop dinging his credit so you two can make a financial move together. But ask yourself, again, why the collection agencies are calling. Is it due to his bad luck? Or bad decisions?

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For day trading: Never

Unless your partner is a truly, strongly educated man in this matter (and really, even the most skilled people in this often lose) don’t lend him money for day trading. You know what—just don’t do that.