31 Questions You Should Ask Your Significant Other

Talking about money with anyone (even yourself) can be awkward as hell. And it gets even more complicated when you’re having the conversation with the person you’re sleeping with.

I don’t remember my earliest conversations with my husband, Ken, about money. We must have talked about splitting the bill in those early days of dating (just out of college, both totally broke), but I do remember the first time we discussed a big purchase. At the time, he was in a band. I was visiting family in Texas, and Ken called to ask if it was okay if he spent $200 on a bass amp. We’d been talking about moving in together, but hadn’t taken those steps yet. I was thrilled when he consulted me. I took it as a sign that he was serious about the relationship. (For the record, neither of us can remember if he actually bought the amp; the band has long since broken up.)

In the years since, we’ve had hundreds of conversations about money. But even if we don’t always agree, I really like talking with Ken about our finances, because those talks are necessary for planning our future together.

Launching into those conversations can be tough, though. When is it appropriate to have that first conversation about money? Refinery29 financial advisor Priya Malani and I talk about this a lot, and during one chat, she mentioned a client who had a list of 40 questions she asks potential boyfriends. I was immediately intrigued: I had to see that list. And then I wanted to figure out if we could turn this list into something money-focused.

In the end, we trimmed the original list from 40 to 20 questions, and then we added 11 more financially-conscious questions that we think are essentials. Ahead, we walk you through eight major relationship milestones. But here’s the thing: Everyone is different, and some of these questions might not apply to you, you might word them differently, or you might ask them at a different stage. Focus less on the milestones and more on the questions.

The next big issue is when to ask. That’s also a personal matter. I like to talk about money away from home, over drinks or dinner. For other people, drinking and money can be a terrible combination. In the early stages of a relationship, you’ll have some trial-and-error as you try to figure out the ideal time for these (sometimes) difficult conversations.

And don’t feel bad if it makes you feel uncomfortable. Priya and I aren’t saying it’s easy, but we are saying it’s necessary. Yes, it’s scary and awkward, but money powers your future, and there are few things more thrilling than planning a life with someone.

So make a date, and get ready to start talking.