Wealthsimple is a whole new kind of investing service. This is the latest instalment of our "Dear Ms. Etiquette" series, where our columnist untangles the issues that happen when people and money get together.

Dear Ms. Etiquette: Ready for a tech-era money problem? So last month I was invited to a friend's birthday party. “I found this rad flat in Barcelona. Come and hang!” it said. I went! I hung! It was a cool way for me to take a trip I wouldn't have been able to afford — my friend is far wealthier than I am. But then, a couple weeks later, she whatsapped for my share of the flat, which was actually an Airbnb. Is that fair? Help!

Yours, Reluctant Renter

Dear Reluctant,

It's been a couple of years since digital challenger banks like Monzo or Starling and services like Splitwise - began playing a role in our day-to-day interactions. Like many other innovations, the ability to split costs through an app was designed to make our lives more convenient. And they have! A generation of waiters go to sleep each night grateful they don't have to divide a dinner cheque by eight and then process a stack of debit cards just because someone had a birthday. The notorious friend who “forgot their wallet” has fewer excuses not to pay you back. Or how about this: Last summer, on holiday, a man at the beach attempted to sell me a nice IPA. As I was scrounging around for cash, he suggested I pay him via Square instead. The future had arrived, and the beer tasted that much more delicious. Eat your heart out, pound coin.

But like many technological tools meant to make life more convenient (have our lives gotten too convenient? Has convenience itself become inconvenient? Topics for another column), payment tech has introduced a whole new set of complications.

Why? Partly because even when it's “digital repayment,” it's still a money transaction between friends, neighbours, colleagues — and those are bound to be weird. Partly because apps promise to replace the need for awkward in-person conversations about who owes what, which often should require an awkward conversation. And mostly because payment tools in apps can be an excuse to send a passive-aggressive notification asking people to pay you.

Just know, Reluctant Renter, you're not alone. I know a guy who tried to kiss a girl on New Year’s Eve, was rebuffed, and then sent her a bill for an evening’s worth of expenses on January 1.

But don't despair. It really comes down to human decency, which, unlike payment apps, has been around for more than 10 years. So let's start with the basics*.*

When is it OK to send a friend a digital bill?

It's a little like sex: As long as everyone is up-front about what they want, what the rules are, and gets permission, digital repayment can be wonderful. If you're out with a big group that had way too much fun (aka booze) to divide a bill without inducing a preemptive hangover, then, for god's sake, throw a single card down and divvy up the bill via some bank transfers! But be explicit about it: “You guys, transfer me money tomorrow — I'll tell you how much.”

It's also way more civilised than trying to do maths at a bar at 2 a.m.

Same goes for a dinner among friends. Is there a credit card points monger among your party who wants to get the bill? Go for it. Just let everyone know your intentions, and send a request for repayment promptly, while the transaction is still fresh in everyone's memory. We eat three meals a day! It can be jarring to receive a £50 charge for a stray dinner three weeks after you ate it.

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A good way to know if it should be a chargeable event or an un-chargeable one is to think about the venue. Anything outside the home is fair game for a split expense. If someone suggests lunch at The Ritz in London, but you are living on a Greggs budget, you better decline unless you're ready to foot your share of the bill. Once someone invites you into their home, however, all obligations of equal payment are off unless explicitly discussed.

When you invite people to your house — for dinner, for a game, for a drink — you are essentially entering into a contract in which you alone will absorb the cost of refreshments and food. Should your guests come with something — a dish, a bottle of red, an offer to pitch in? That's the right thing to do. If they don't, you do have the right to never invite them back, but you don't have the right to send them a request for £7.64 for “nacho ingredients.”

That is, UNLESS — say it with me now — you tell everyone they're splitting the cost ahead of time. Consent is key. If you didn't ask permission to send a digital bill (or receive an answer), keep your thumb off that request button. With great repayment power comes great responsibility not to be an insufferable jerk.

When is it never OK to send a request for money?

OK. First rule: Encounters with strangers — specifically dates — are completely off-limits. No excuses, sorry. Unless your date literally stole money from you, you may not ask for £15, even if she ate all the chips. And doing so is an act not just of aggression, but of cowardly aggression. If you're mad at your date, you can write an email expressing your feelings. Or, better yet, take a yoga class and move on. But don't be Splitwise-aggressive about it.

Of course, it's OK to go dutch; you just can't do it retroactively. But you should announce your intentions well before the bill comes. A simple: “Hey, let's go dutch tonight so no one's weird about money!” is permissible.

My second piece of advice is for all those people who are both forgetful and perpetually cashless? If you invite someone to a meal—platonically or not—and don’t have a way to cover your share, take the initiative to pay your dining partner back. Any other behaviour is rude, manipulative, and never charming (not even when artsy beat poet types like Jack Kerouac do it).

It's also wise to avoid sending a request when you never told anyone they'd be responsible for paying. This, Reluctant Renter, is what happened in Barcelona. Big fancy Airbnb. She should have told you up-front not only that you'd be responsible for covering your share, but exactly how much that share would be. Otherwise, you can't make an informed decision.

When is it OK to assertively send an un-asked-for payment?

There's an important corollary here: when someone aggressively pays for you and you don't like it. There are stories making the rounds, like one about a male coworker who invites his female colleague to “work drinks.” Then, in an attempt to turn those work drinks into something more romantic, he grabs the bill. In that case, it's OK (actually smart) to send a message by repaying your portion of the bill via a quick transfer.

So how do you deal with someone who overdoes it with the repayment requests?

First off, say something — preferably when neither of you is drunk. Put yourself in their shoes/wallet. Who knows what’s happening in your friend's mind or bank account. One option is just to let the offending party know that it's not cool to request money from you after the fact. Try something like: “I know sometimes it's a drag to figure out who owes what when we're out, but I'd love a heads-up whether a round is on you when you're ordering.”

One important point: It doesn't matter who has more money here. This is about human decency and kindness and respect. We don't live in a society wherein whoever has the most money must be the one who pays for every meal. We live in a society where people should be open about who is paying for what, or you're being a jerk. You should never couch your disapproval in the fact that you're broke — that's not the issue here. And you should never accept “Well, you have more money, so it's fine” as a tacit argument.

Let's get back to you, Reluctant Renter. IMHO, the best way to handle your situation is to send her a note: “Oh no! I had no idea we were splitting the cost. I didn't even know what the cost would be. And I don't actually have the money. How can we work this out?”

If she insists, it's time to decide whether you want to eat the cost or risk losing the friendship. If it's part of a pattern of passive-aggressive behaviour, ask yourself: Do you really need friends like these anyway?

And if you find yourself really really angry about this or any other digital repayment etiquette, it may be worthwhile to ask yourself why you feel that way. Is it because it makes you feel like your friendship is transactional? (That's a valid reason; say so.) Does it take the fun out of seeing your friends? (Ditto.) Are you secretly bitter that some of your acquaintances are financially better off than you? (Let me tell you, Reluctant Renter, I am! But I know that the fact they make more money than me isn't their problem — the bitterness is my issue.)

Ultimately, all of this comes down to knowing how to — not to mention, being willing to — talk about money. It may feel decidedly uncool or uncomfortable at first, but it's a necessary life skill. And no amount of technology can make it go away.

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