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How to Talk Finances When You Want Your Love (and Money) to Last Forever

Man and woman laughing together
Stephanie Bolling and Ian Sasseen spend some time outside of their prospective offices in downtown St Petersburg. Carmen Mandato/The Penny Hoarder

Our first money talk started with pad thai.

I was on a first dining date — our actual first date was playing shuffleboard — with a new guy named Ian. When the check came, I instinctively pulled out my wallet and offered to split it. He chased away my offer with his Visa.

I felt slightly embarrassed for my reverse chivalry. It’d just been my modus operandi for years with friends and past boyfriends. Had I overstepped a money boundary on one of our first dates?

Back in the car, Ian admitted he thought the opposite. In fact, he liked my lack of expectations.

Turns out, his ex was all about money — his money — and my simple gesture became a catalyst for future conversations about our finances.

That was 2015, and it was only the beginning. Ian proposed to me last Christmas, and I said “yes.”

Now we’re having even bigger talks about our finances and future while also planning a wedding and honeymoon. We even signed up for our first joint credit card and are warming up to the idea of shared bank accounts.

5 Money Talks That Made Us Financially In Sync

Female and male walking holding hands
Stephanie and Ian find that simple gestures go a long way in communicating with each other, especially when it comes to their finances. Carmen Mandato/The Penny Hoarder

In the beginning, I wasn’t used to talking so squarely about money. To me, money talks always wore kid gloves and bore a “no trespassing” sign. My instinct was to tread lightly. Funny how that instinct got turned on its complicated head with one card flip.

Here are a few of the money talks we’ve had since the pad thai incident.

Are You a Spender or a Saver?

We didn’t talk money much during our first six months of dating, but one thing was obvious: He was a saver, and I was a spender.

I learned his mom used to be an accountant, which made him predisposed to saving. Meanwhile, I haven’t always been the best with money. It’s taken a lot of sacrifice, commitment and wading through debt to teach myself good financial habits. Even still, I struggle.

Our spending habits came up gradually when I gleefully exclaimed that I’d paid off a credit card, or by way of a package on my doorstep from a splurge at Shein or Amazon. Surprisingly, Ian didn’t scold or guilt me for spending. In fact, he agreed you have to treat yourself sometimes, or that splurge could turn into a spree.

His uncritical attitude made me feel more relaxed and less guarded about my spending habits.

The Dreaded Salary Talk

Eventually, my splurging and his saving gave way to conversations about how we manage our finances… and how much we make.

We’d dated for over six months and built enough rapport to divulge in these sorts of money talks. Sure discussing salaries can be awkward, but the timing felt right.

Sidenote: If your partner makes six figures, try not to let your jaw drop or use the info to make them always pick up the tab. And if your partner makes a low wage, be understanding and create a safe, loving space for them.

How Do You Manage Your Money?

I’d always paid my credit card when the due date came. Ian, on the other hand, made weekly $20-$40 payments that often added up to more than the minimum due.

“Duh, why hadn’t I thought of that?” I thought. I quickly changed the way I paid off my debt and felt grateful we were talking seriously and constructively.

Within a year of dating, I took out a personal loan to pay off some debt. I told Ian about it, but I didn’t ask for his input. These were my finances. He was encouraging about it and admired my financial initiative.

Are We Really Ready to Move in Together?

Knowing each other’s salaries really helped when we made travel plans — and when we toyed with the idea of moving in together.

Many of our friends had moved in with their significant others within a year of dating out of convenience and financial circumstances.

We embraced our independence but enjoyed entertaining the idea from a safe distance. When the topic of our friends’ follies came up, we used it as fodder to hypothesize about what we would do in that situation, including how we might split bills.

That speculation spurred more talks about the big “d” word: debt. Let’s just say it’s definitely easier to talk about how much you make than how much you owe.

He’d known about my loan, but not everything. I knew he had student loan debt, but not everything. It was clear that before moving in together, we needed to talk about everything.

And we did just that. Being better informed about each other’s finances helped us better determine what we could afford.

How Will We Split the Bills?

By the time we finally moved in together after two years of dating, we’d already established a divide-and-conquer strategy toward bills. The internet, HBO and the Ashley Furniture credit card are now in my name, while electric, water and the Lowe’s store card are in his name.

We even entertained the idea of a cleaning service, which forced us to sit down and discuss the pros and cons from money to time management. We decided that $20 each a week was worth it for both of us.

When it comes to going out, I still offer to pay sometimes — and guess what, he lets me. He finds it attractive, but he does pay for me way more than I do for him. Generally, I handle the cheapies, and he gets the fancies. Partnership.

Money Talks to Come: Lessons From a 31-Year Marriage

Male and female sitting in a booth
Ron and Leslie Christon have been married for 31 years, and talking about finances is a big part of their partnership. Carmen Mandato/The Penny Hoarder

I feel pretty confident about our progress so far, although, realistically, we still have a lifetime of complex money talks ahead of us. We have yet to buy a house, say “I do” to the other’s debt, or bring kids into the equation.

I reached out to Leslie Christon, my first boss out of college, for some help navigating our uncharted financial territory.

She and her husband, Ron, probably have more financial coolness than any couple I’ve known. In 31 years of marriage, they’ve lived in four states, owned four homes, had a son and worked 10 jobs between them. They recently opened a restaurant, Chica’s Taco Bar, in Clearwater, Florida. And they’re still married. Can I get a “cheers” for that?

When they met, Leslie already had a house and two cars: her sports car and a work vehicle.

“I think Ron appreciated my independence,” she said. “He didn’t have to carry the burden alone.”  

They didn’t need each other financially. Instead, they chose to be with each other. That created a solid foundation, allowing them to build trust and pool their resources.

So that was some validation that Ian and I might just have this whole money thing right… Might. Here are some other pointers Leslie gave me about financial communication.

Tell Your Partner What You Want Your Future to Look Like

Leslie said she and Ron couldn’t have made things work without some core values that make every endeavor easier.

“When you realize there is a permanence in your relationship and you’re going to move forward together — whether it’s living together, getting married or having kids — you commit not just emotionally, but you commit financially, honesty and truthfulness,” she said.

She and Ron both wanted kids, so they discussed everything from medical expenses to a college fund. They even started a general savings plan for their son after he was born and used it to teach him the value of saving money by matching every dollar he put into it.

Divulging their hopes and dreams helped them avoid many conflicts and roadblocks because each knew the other’s intentions and expectations every step of the way.

Money talks
Leslie and Ron take a moment together in a booth at their restaurant before the lunch rush begins. Carmen Mandato/The Penny Hoarder

Don’t Forget to cc Your Spouse

One of Leslie and Ron’s greatest successes came by accident.

Due to conflicts with work schedules, they swapped who was responsible for paying bills. The switch gave each one perspective on how much money was coming in and going out. They now alternate the role of bill payer every couple years as a best practice.

Knowing each other’s passwords and security questions facilitates this practice. Not to mention, there’s never any worry about a secret credit card or savings account.

This is good because, according to Go Banking Rates, being secretive about finances is the No.1 financial deal breaker for couples in the U.S.

But it’s not always peaches and cream.

“We have our spats like any couple,” Leslie said.

She admits those usually happen when she goes shopping or makes a big purchase without telling Ron — even if it’s for a vacation or a present for him.

(Note to Ian: I would never be mad if you bought me a vacation.)

Show Your Support With Talk… and Action

When Leslie began to consider opening a restaurant, she and Ron did heaps of discussing, projecting and planning before making any big moves. They hashed out a budget and factored in every possible expense — all a year before opening Chica’s Taco Bar in late 2017.

And did I mention Ron maintained his career while helping Leslie with the endeavor? Oh, and he also had to agree to rein in spending on non-necessities. Each had the other’s back through the thick stacks and the income trickle.

So far, it’s a success, thanks not only to their well-crafted business plan, but because of their financial forwardness over the years.

“We trust each other implicitly. I trust him financially and he trusts me financially,” Leslie said.

What Our First Money Talk Taught Us

I think back to the pad thai incident and how it shaped our healthy financial discourse.

Ian said that, in retrospect, my attempt to pay told him, “I’m in this with you not just because you’re providing, but because this is a partnership.”

With that, we agreed that the road to our financial future would be a two-way street, and we’d each have to pull our own weight and make it fair.

And we’ve been partners ever since.

man and woman holding hands
Stephanie and Ian found full disclosure brought them closer together more than it pushed them apart.  Carmen Mandato/The Penny Hoarder

Stephanie Bolling is a staff writer at The Penny Hoarder. She plans on solving all her financial fretting by asking Ron and Leslie to adopt her and Ian by proxy. Just kidding. She just wants to fast-forward to the honeymoon.

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