There’s no perfect time or  foolproof way to talk numbers with someone you’re dating—but there are some times and approaches that are straight-up better than others.

Beyond the common-sense stuff (literally no one wants to discuss how much they make on a first date; never bring up money issues in the middle of an unrelated fight), how can you strike up the money conversation with your S.O. without stepping on any feelings or triggering a totes awkward moment?

It’s a question I get asked a lot as a personal finance blogger, so I decided to speak to two women who had very different (but very very open and very productive!) conversations about money with their partners. Here’s what I learned.

Keep it simple

Don’t blindside the person you’re dating with a Big Financial Talk that touches on a gazillion different issues. Instead, take a page out of Hailley Griffis’s playbook and start with just one topic. The Toronto-based communications specialist, who works at social media management site Buffer, had only just started dating her bf when she decided to talk about her salary and ask about his.

“I met him at a wedding in Ottawa, and we totally hit it off. He’s in the American army, and he was like, ‘You should come to Arizona next week and hang out with me,’ and I was kind of like… well that’s very forward,” Griffis says with a laugh. “But I really liked him, so a week later I showed up in Arizona. It had already come up that I work for a tech company, and I mentioned salary transparency, since our salaries at Buffer are all online. What was really interesting is that he was just like ‘OK,’ because the military salaries are all based on a public grid anyways.” 

Since both Griffis and her guy didn’t have any qualms about disclosing their incomes—in fact, Griffis’s salary lives in an online spreadsheet for the world to see!—this initial money talk was easier than most. You and your partner might need to work up to sharing those details, but it’s important to do so no matter what.

Think about all of the spending that goes along with a new relationship, from dinners out to weekends away. You can use any one of those fun adventures as a way to casually bring up cashflow (“Hey, since we hit that fancy restaurant last weekend, are you cool with making dinner at home and Netflix tonight?”).

Because yes, that totally counts as a first money talk—and if you don’t start having them, by the time you get around to bringing it up, one or both of your credit cards is going to be in serious pain.

Open up about smaller decisions until you’re ready to talk about major #goals

If you’re thinking that those small conversations about what you’re going to eat are a far cry from Having a Money Talk, think about how much easier it’ll be to make joint decisions when you can speak openly about what you can afford. It’ll impact everything from where you go for brunch to how you decide on joint vacays.

When Griffis and her boyfriend were talking about where to take their first vacation together, they had to get real about what they each could afford.  

“We just bought plane tickets the other day, and it was like ‘OK, well, we can afford $300 each,’ and it was just a very open conversation around what we can afford right now, since we know how much we both make,” she says. “It helps us make those travel decisions, especially since we’re long distance. It helps us split it more fairly.”

That’s the real incentive to opening up with your partner about money: being able to share things fairly. With all the joint spending that happens in a duo, it’s important to talk about those decisions, but there’s only so far you can get without any context.

Like sure, maybe splitting everything 50/50 sounded great at the start, but when you realize you make triple what your partner does? That information might change the conversation a bit, which is normal.

Chances are, you’ve probably got a ballpark idea of how much your partner brings home already by looking at his or her lifestyle—and if you’re way off the mark, well, that’s an entirely different conversation.

Be upfront about debt

Getting a clear idea of salary numbers and being open about small money matters is important, but there are a lot of other money-related matters to cover once you start making financial choices as a team. That’s what Samantha Hartley, an independent consultant based in Ottawa, found out when she decided to talk about her debt load with her boyfriend.

“When Rob and I met, I had all my debt, all my student loans, my car debt and everything,” says Hartley. “It was a couple of months in, where we kind of knew we were getting serious, and I totally trusted him. That’s why I had no shame and was like OK, he’s either going to know where I’m at and he’ll accept it and we’ll figure it out—or you know, if he doesn’t like it, and he’ll leave.”

Once everything was on the table, Hartley and her boyfriend were able to make decisions together with full information, including the all-important question of whether to rent a place or buy one.

In the end, they decided to rent, which gave Hartley the flexibility to tackle her debt and pay it off on her own—but the open discussion got other things on the table, too, like what neighbourhood they wanted to live in.

That’s the kind of openness and joint decision-making you want—TRUST ME—and the only way to get there is to be honest. It can be scary, especially if you’re coming into a relationship with debt, or you feel like you and your partner’s money situations are wildly different, but working up to a real-talk moment is the only way to move forward.

Talk as a team  

Now that you’ve got everything on the table, you can get to the fun stuff: tackling money goals as a team. Which, to be honest, might require some adjustments on both of your parts.

For Hartley, the decision to rent wasn’t the only thing that came out of her debt disclosure. It also had a big impact on her spending patterns—fewer $50 manicures, more grocery shopping—as she and her guy looked toward the shared goal of eventually owning a place.

“The accountability of having a partner is huge. If you feel that your decisions are impacting someone else or impacting an outcome, it makes you take it more seriously and that was a big shift for me, because when I was single my decisions didn’t impact anyone but me,” says Hartley.

If you want to move forward as a team, and work towards some of those big, expensive life milestones like owning a place, having a fancy wedding, or taking a round-the-world vacation together, you’ll need to be clear on the numbers—and what you’re both willing to do to make it happen.

And pro tip: This isn’t the kind of conversation that happens once. If you’ve got a big shared goal on the table, make sure to check in every few months on how things are going. You never know when feelings or expenses can get in the way of what seemed like a crystal-clear plan.

Ultimately, no matter the financial issues you might be facing, the financial decisions that matter most to relationships all involve your shared goals. The right time to start opening up about your financial deets is whenever you realize you’re going to be making joint money decisions with another person.

And hey, if that just happens to be on the first date? Power to you.

Filed under: flare, lifestyle