How to Deal With That One Friend Who Always "Forgets" Her Wallet

Petty Cash is a weekly advice column where the experts (plus a millennial InStyle editor well-versed in pettiness) weigh in on your awkward and annoying financial faux pas.

DEAR PETTY CASH,

So, I have this one friend.

I love her, I really do — we’ve known each other for years, we have a lot in common, we always have a great time together. She just has one major flaw, and that’s when we go out for drinks and dinner, she always conveniently “forgets” her wallet, her credit card, her cash, or all of the above. The excuses she’s come up with are actually impressive. Once, she literally told me that she “thought her wallet was stolen on the way to the bar.” It really stuck out to me, because she didn’t seem upset at all, and never brought it up again. At this point, I’m fundamentally certain she just never wants to pay.

What should I do?

BEFORE we get down to brass tacks, I’d like to do the thing that insufferable people do and play devil’s advocate.  It is possible to be this forgetful of a person — believe me, I know. I’ve spent my entire life forgetting things: my phone, my keys, my sunglasses, and yes, my wallet. I’ve been that friend on more times than I can count, and to anyone reading this who has that friend, I urge you to be kind to them. They are doing their best. If you are that friend, well, be kind to yourself. Additionally, please learn how to use Venmo.

However, your friend seems to go above and beyond the average scatterbrain and into territory that is straight shady. That’s not to say she’s being malicious, but her increasingly elaborate excuses seem to imply that there’s something going on you may need to explore. Figuring out what the “something” is, though, is the hard part. In an ideal world, you’d simply be able to have a conversation with your friend, call her out on her weird bullshit, and move along with your day. Unfortunately, these situations are rarely so cut-and-dried — and often, they take several conversations to attempt to resolve.

According to sex and relationships expert Megan Stubbs — who consults on everything from dating red flags to building fulfilling relationships (whether that’s cultivating openness among friends, or making sure your partner orgasms) — the key to navigating this successfully is to start by asking the right questions.  

“It seems that a larger issue may be at hand here,” Stubbs says. “Talk to your friend and see what is going on. Are they going through something? Is money tight right now?”

Simply asking what’s going on might seem obvious, but you’d be surprised how easy it is to gloss over an issue between two people by simply avoiding it. You say your relationship is otherwise tight and mutually fulfilling — if that’s true, your friend may feel comfortable answering you in an honest way.

If she’s open to discussing the issue and ultimately finding a way to solve the problem, a clear arrangement before you go out together could be the answer. You could plan to do things that don’t necessarily require money: Instead of meeting up at a bar, you could hang out at your place or hers. Giving your friend the option to pay you digitally at a predetermined time (think PayPal, Venmo, Square, CashApp) could take the pressure off of her remembering her wallet or, depending on what’s she’s going through, having the money on hand right then and there.  

Ideally, a conversation is all it will take to begin repairing the damage done to your relationship — and hopefully, that means she’ll begin paying her fair share when you hang out.

But let’s say it’s not that simple. Perhaps your friend can’t give you a good answer, or refuses to. Then, Stubbs says, it’s time to draw some hard lines.

“If this is a constant occurrence and your friend has no excuse, have a sit down with them and explain that from here on out, you will not be picking up their tab anymore,” she says. “Explain how it makes you feel taken advantage of and is an unfair expectation. Using ‘I’ statements helps shift the blame solely from them, and it centers how this recurring situation is making you feel. In an ideal situation, your friend will listen to you and hopefully will agree to be more mindful about leaving you to pick up everything.”

And if things go from bad to worse — meaning, your friend doesn’t respond well to the confrontation, or respect your boundaries — it might be time to reevaluate what they are actually bringing to the table.

“Maybe it’s no big thing to you, and you will continue to keep this person in your life,” Stubbs says. “Or maybe it’s time you cut ties. The answer isn’t yes or no. Think about what this person brings to your life. If the goods don’t outweigh the bad, it may be time to part ways.”

Sure, you may have a lot in common and have fun together, but if this friend can’t hear where you’re coming from, it indicates a concerning lack of respect for your boundaries, and, to be quite honest, your bank account. In other words, real friends don’t make friends feel uncomfortable every time they hang out. If your friend is fine with doing that, it may be time to cut your losses.

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