The 20 Money Questions You Should Ask Your S.O.

Illustrated by Seung Won Chun
In the game of playing hard-to-get, money is the clear winner. Not surprisingly, it remains the number one cause of break ups amongst U.S. couples. Yet even though we know this, many of us still avoid money talks with our S.O.s — after all, it can be awkward and uncomfortable at best.
I remember one of my first money conversations with my husband: It was my 21st birthday and some friends and I were flying to California to celebrate. My husband (who was then my boyfriend), flat-out refused to come. Pissed, I confronted him and demanded to know why. Calmly, he explained that flying cross-country wasn’t an expense he could afford and that we’d never really discussed it together.
The thing is, he was right. It was an important moment in our relationship — a realization that we couldn’t take each others’ finances for granted.
From then on, money came more into focus for us as a couple, and that experience was the start of many others. It came up when buying plane tickets to maintain our long-distance relationship. It surfaced when we moved in together, and again when realized we had different spending habits. It manifested itself through fears we didn’t even realize we had until we got our first joint credit card — on my credit. Each of these stories made me wonder if other couples struggled through the same challenges.
Those experiences led me to found Zeta last year, a tool that helps young couples master money together. Through a combination of technology and advice, we give couples the ability to track, manage and master their finances together. Over the past 5 years, I’ve talked to hundreds of couples and coached many of them on how to navigate their shared finances.
I’ve heard it all: from couples who are hiding accounts from each other because they’re scared of their debt, to two-somes who are totally crushing their goals. I’ve met a couple who created 23 accounts to organize their finances, and others with just one account and less than $100 in it. There are also couples who are hacking the credit card points game (a tricky practice known as “churning”), to those navigating prenups and negotiating their first home. This research has taught me a lot about what works, what doesn’t work, and where couples get into hot water.
But talking about money doesn’t have to be so uncomfortable. I took the insights I learned after talking to so many couples and used them to write the 20 questions below. These questions are less about digging up dirt on each other and more about finding a fun, easy way to start (or continue) your money conversations.
Fun fact: couples who have regular money conversations report being twice as happy as those who don’t. Who doesn’t want to laugh more and worry less? Have fun and tell me all about your experience in the comments.
1. Grab your partner, your favorite drink and find a comfy spot for an uninterrupted conversation. I highly recommend you put your phones away and sugar is always optional.
2. Read each question out loud and take turns answering it with your SO.
3. The questions are broken into three sections, representing different stages of our lives. Each section should take no more than 15 minutes.
4. If any of the questions feel too heavy, skip them! It’s less important to answer everything and more important to just get the conversation started.

More from Work & Money

R29 Original Series