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Friends are the best. You can tell them anything and everything. They know all your secrets along with your ups and downs. Well, except when it comes to money. Finances can potentially make or break a relationship. People have a tendency to want to tiptoe on eggshells when it comes to that topic. Below, we’ve mapped out some potentially awkward money manners type situations along with what to do to get past them.

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You bought your top from the “Last Chance, Double Coupon, Return Pile, Ultimate Clearance” pile, and you don’t want people to know.

My biggest nightmare: when a friend exclaims “OMG I love that, where did you get that?” and it’s from the “we’ve marked this item crazy low because we don’t want to pay for the shipping to dispose of it” rack at TJ Maxx. But fear not, the truth is that your friend likely is just trying to pay you a compliment. If you really want to dodge this money manners question, try pivoting. Say “Thanks! It’s been in my closet forever so I totally forgot I even had this.” Have you ever done that before?

Your friend probably can care less how much you paid for your shoes. By asking you where you bought something, they’re likely trying to say, “That’s such a great look on you! How can I look more like that?” Try a combination of pivoting + suggesting a place where they can achieve a similar look: “I think I got it while I was traveling, but Anthropologie has so much cute stuff on sale now, have you checked out their sales online yet?”

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You have a friend that’s a — doctor, CPA, attorney, graphic designer, professional chef — and you’d like their expertise. Are you expected to pay them?

Uhh, definitely. I cannot emphasize this one enough, pay your friends for their work. If anything, pay them more than full price because if they’re a real friend, they’re giving you more than full price service/advice. Make sure to be the one to bring it up first, try saying, “Before we go any further, how should we do this to make it official? Did you want to draw up a contract or maybe just shoot me an email laying out the payment terms?” Do not let them take no for an answer, this way you won’t fall out of your chair when a bill arrives at your house.

If your friend just offers you pro bono advice or say designs your start up’s logo for free then come up with a creative way to show your appreciation. Get them a gift card to their favorite store, send them some nice flowers and a card, or take them to dinner at their favorite restaurant. People do nice things without expecting anything in return, but make sure to do your part by paying it forward.


You loaned some money to your friend. She’s yet to pay you back but the next time you see her she’s wearing a brand new $500.00 jacket. Do you say something?

You should say something. Definitely don’t keep it to your self and then resent them behind their back. But make sure to tread lightly until you have all the facts. That jacket might have been sitting in their closet from last year because they bought it offseason and now they finally have a chance to wear it. (Story of my life) The jacket might be a gift from a friend who works at the store. Or they might even be ready to pay you back, just haven’t a chance to go to the bank yet that day. Wait until you have the full story before you say squat. Trust me.

If none of those possibilities are the case then you still should say something. Just be honest but gentle. Remember if your friend had to ask you for a loan, they’re currently in a very vulnerable place. Try saying, “Hey, I hope everything’s ok. I just noticed that you haven’t had a chance to pay me back just yet. Are you still having a hard time getting back on your feet?” If they become angry and/or defensive then just forget it.

Just keep in mind that loaning money to a friend 50% of the time means that it was a gift and you’ll never see that cash ever again. Be sure that you’re in a secure enough financial place that you’ll be OK if you never get the money back. Also, it’s OK to say “no” when someone asks you for a loan. You’re not obligated to take on anyone else’s financial burden.

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Your broke friend never has any money but still wants to go out all the time. Are you expected to pay for them all the time?

No, you are not. Do not let someone else’s financial burdens (and lack of money manners) stop you from living your best life. Instead, try to include your cash-strapped friend by coming up with activities that cost little to no money — potlucks, hiking, picnics, hanging by the pool.

However, if they have a tendency to show up to events with no money and expect that someone else will pick up the check, you need to be blunt. Try saying, “Hey girl, I know you’ve had a rough couple months so I can spot you again, but we’re going to have to start going to Mcdonald’s or something soon if this continues. You know what I’m saying?” If their behavior still continues, just text them ahead of time that you cannot pay for them if they decide to go to the dinner. Remember, it’s not your responsibility to financially support your friends.

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You’re traveling on a group trip. You made the reservation for the block of rooms and put it on your credit card. Now there are some stragglers who’ve yet to pay you back. How should you ask for the money?

Let’s keep it real. Your broke friend from the previous question always winds up going on this trip. In this particular case, you’re not loaning cash-strapped friends any money. Anyone who’s too broke to afford their share of the hotel shouldn’t be going on the trip anyway. This is where you can be super blunt.

Try sending out a group text to everyone on the trip saying, “Hey, just put the reservation on my card, everyone owes me $258.95, can you ladies just confirm once it’s been Venmo’d back to my card? Thank you, don’t forget the bikinis!” Having to visually see in the group chat who has paid you back and who hasn’t will put the pressure on any laggers from procrastinating to pay for their share.

It’s also perfectly OK to send a Venmo request right after you’ve put the charge on your credit card. Wait a couple of days and then send a follow-up text to your group chat “Hey, these are the people who have paid for their share of the hotel, all my procrastinators can you make sure you’re not late for the plane as well? Thanks LOL.” Keep it light but keep it real. Just like our motto.

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