Wealthsimple is a whole new kind of investing service. This is the latest installment 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 house in Palm Springs, California! 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 me. But then, a couple weeks later, I got a Venmo request for my share of the rental payment for the house. Is that fair? Help!

Yours, the Reluctant Renter

Dear Reluctant Renter,

It’s been a whole 10 years since the mass adoption of mobile peer-to-peer payment services: Venmo, Square, Chase Quickpay (for those of you who suffered through that phase of innovation), and whatever launches tomorrow. Like many technological things, these tools were 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 check by eight and then process a stack of credit cards just because someone had a birthday. The purveyors of garage sales and lemonade stands can now press you for a sale even if you tell them you don't have cash. Or how about this: Last summer, a man on the beach attempted to sell me a Corona. I told him to wait while I ran to the ATM, and he said, “You can Venmo me.” The future had arrived, and the beer tasted that much more delicious. Eat your heart out, Alexander Hamilton.

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), the convenience of being able to pay your friends on your phone 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, neighbors, 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 Venmo can just be an excuse to use a push notification to be passive-aggressive about 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. Someone told me about the host of a dinner party who waited until everyone left and then sent them all a request for the cost of the meal, pro-rated based on how much wine each person drank.

But don't despair. It really comes down to human decency, which, unlike Venmo, 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 apps 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 on Venmo! But be explicit about it: “You guys, Venmo me tomorrow — I'll tell you how much.”

It's also way more civilized than trying to do math 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, even more so when that dinner is represented by a single martini emoji.

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 Eleven Madison Park in New York or Canoe in Toronto, but you are living on a Sweetgreen 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 six-pack, 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 “nachos 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 charge 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 cheese curds. 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 Venmo-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.

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 Palm Springs. Big fancy house. 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 Venmoing the guy your portion of the bill.

So how do you deal with someone who is a Venmo creep?

First off, say something — preferably when neither of you are 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 spring a request on 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 behavior, ask yourself: Do you really need friends like these anyway?

And if you find yourself really really angry about this or any other Venmo 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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