Shared experiences are a big part of friendship, but as you and your pals find romantic partners, have kids and pursue careers, the opportunities for road trips, lost weekends and even just one-too-many on a Wednesday start to diminish. Nothing will replace those moments, but you can keep the intimacy in a friendship alive, and even deepen it, by discussing important matters that reveal unknown aspects of your life and personality. By which we mean: talking about money.
Unless you live in a commune, money is significant in every aspect of your life, and discussing it can bring you closer to your friends, and sometimes provide practical help along the way. Obviously, you should proceed with caution, and be prepared to divulge the same things you ask about, but with those rules accepted, here are some conversation starters that can lead to relationship-strengthening discussions.
You already know where your friends live, how they spend their free time and what they do for money (except for that one guy who lives near DC, travels abroad for work and mentions non-disclosure agreements when you ask where he’s been), but you discover a new side of someone when they tell you what they’d do if they won the lottery, or became never-work-again rich by other means. Some people have hidden passions (“Oil painting and bass playing, you say? Full time?”) or surprising charitable instincts (“You like animals enough to donate how much?”). Others turn out to like their current situation less than you knew, such as friends who seem happy living in the middle of town but would actually move to the countryside tomorrow if they could earn a living there (or had no need to do so). And there’s always one friend who would leave their spouse if they were richer.
The other kind of “What If…?” may be less jolly, but it’s no less important: “What would you do if the worst should happen?” Does your friend have end-of-life plans? Life insurance? Do you? Sharing your plans and strategies will be useful to both of you. These are conversations about an imagined, improbable future (whether that means winning the lottery, or a catastrophe taking place) but they shed light on the reality of how someone feels about their life now, deepening your relationship in the process.
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“What are your financial worries?”
Sharing fears brings you closer to your friends – doing so requires vulnerability and trust. It’s also good for both parties: The person who talks about their fear feels unburdened, and there’s a good chance the listener will hear something familiar – a worry they recognize, which feels less overwhelming when they realize others have it too. You might start by saying, “I’m worried I won’t be able to afford a house/put my kids through college/retire/all of the above – you?” Such conversations can lead to solutions – an outside point of view can include useful suggestions. This line of discussion is also a great leveler: everybody worries about money, even the rich. Just remember to bite your tongue if your friend’s biggest money worry is paying for his next vacation.
“How do you and your partner handle money?”
It’s surprising how many different approaches people take to joint finance. Most of us want some measure of fiscal autonomy within our relationship, even if we jointly deal with everything from the mortgage to buying milk, but there are couples that put every cent into a joint account and share all credit cards. Others don’t even want their partner to know if they buy a cup of coffee, and use their joint account for rent, bills and little else, or eschew joint finance altogether. Whatever arrangement your friend and their partner have chosen – or stumbled into – it can be good to blow off steam about it to a disinterested party. If the couple’s incomes differ, does it cause friction? Do they divide fixed costs like rent and bills evenly, or are those pro-rated? And what is each person allowed to spend without discussing it with the other one? (The average American thinks $154 is the right amount, in case you were wondering.)
It can also be entertaining to find out what purchases people hide from their partners, though if you think your friend is hiding money from his wife to pay for his secret family, you may want to skip this one. Does someone have a shoe habit, telling their significant other than a pair of heels or limited edition sneakers were on sale when it was actually just for sale, with a hefty price tag? These kinds of confessions can only bring you closer, as long as you and your buddy are good at keeping secrets.
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“What about your debts and savings?”
People may not be comfortable discussing this, so if it’s a subject you want to broach, you should go first. Saying something like, “What advice would you give a friend who is trying to figure out their retirement strategy/pay down their debts?” will give your friend the chance to share advice without having to discuss their own circumstances. Or you could be more direct about your situation, which may encourage your friend to share theirs (and their methods for dealing it): “I’m trying to save for a down payment, but I’m having trouble putting the money away” is a good start. When it comes to saving, it’s useful to find out people’s strategies and to compare the particulars of 401ks and other options. In the case of debts, people feel less alone when they discover they’re not the only ones still paying off college while trying to save for their own kids’ education, and if that describes you, it’s possible your friend has some good ideas that will help. Friends can be a good benchmark: if they have a similar financial situation to you but are saving a lot more, maybe you need to cut back on sushi or concerts for a while.
“How much money do you make?”
Even in New York City, where it’s socially acceptable to ask someone what they pay in rent before you know their surname, it’s still taboo to ask about earnings. And that’s why it’s important that you consider doing it. It’s a sensitive subject, and if you ask about it you should go first, and make it clear that your friend is not obliged to answer, but it can help both of you make sure you’re being paid what you’re worth. (This is especially important for women with male friends in similar jobs, since female workers are still paid 20% less than men on average.)
If a friend turns out to be earning a lot more than you, they may be able to tell you how they negotiated their salary, and at the very least you’ll know you what should be looking for (plus you’ll both know who should pay for drinks when the check arrives). If you and a friend share this information with each other, you obviously won’t be telling anyone else, and that shared confidence can bring you closer while benefiting you both professionally.
“What’s the weirdest job you’ve done?”
Sharing a laugh is good for a friendship, and even if it wasn’t, this would still be a question worth asking: hearing about jobs you’d never imagined (and which your friend may have no wish to return to) could help you think outside the box if you’re looking for a career change. You may learn that your friend was once a golf ball diver (known as “the most dangerous job in golf” it can make you $100,000 a year), or a copy editor for erotic novels (not as well paid, but considerably safer). Some people have never done anything weirder than babysitting, but if you end up telling your friend about the time you were a tour manager for a rock band, or that summer you spent on a trawler, they’ll end up knowing you a little better, which is what a lasting friendship is all about.
Have fun, it’s not an interview!
If some of these questions seem intense, well, that’s part of the point. (And really, it’s not like you’re asking your friend to produce his last five years of W-9s). The point is that money has been a taboo subject for so long that breaking the silence not only gives you insight into your own financial life, it can also make you and your pals closer. Plus, having these convos can make it less stressful when you and your pals do manage to get together: when you know everyone’s watching their budget, it’s that much easier to skip the swanky wine bar for Happy Hour and opt for some backyard beers instead.
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Michael Davis is a freelance writer and editor who has covered everything from fashion and music to parenting, work, and finance. He has been a chef, restaurateur and record label owner.