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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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