Photo: Daniel Reiter (Getty Images)
In a perfect world, when splitting a check, the bill would add up to a perfectly whole number, everyone would have the right amount of cash and your cheap friend wouldn’t argue about how much of the shared dessert they didn’t eat. Unfortunately, no one carries cash anymore and that cheap friend will likely weasel their way out of paying. Instead of being forced to pick up the check, there are better ways to handle these situations, like small-time cons to combat your freeloading friend’s minor league grifting.
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What literal tricks do you use to micromanage cheap friends? Let us know in the comments!
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Out Skating Cheapskates
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The F*ck You Pay Me
The ol' "I'll pay you back next time" can put you on the spot when it's time to pay. But there are ways to combat this. When the bill arrives, take your phone out and request their half of the check via PayPal, Venmo or Apple Pay. Then wait for them to realize they're going to pay one way or another.
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The Waitstaff Con
If you want to enjoy your life and order whatever you want without paying for your friend, involve the waitstaff. Before you order, excuse yourself to the bathroom. Then slip the waitstaff your credit card and tell them you have to leave early, so charge your card once the food comes out. It's like dining and dashing, but from paying your friend's bill.
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The Spiritual Journey
Next time you see this friend, leave credit cards and tech items at home. Only bring a limited amount of cash. After sitting down, take your money and lay it out on the table so you can both see how much there is. Your friend will ask what you're doing and this is when you tell them, "Oh, I am doing one of those live-in-the-present challenges, and at present I only have $14.86, including tip." Smile, raise your eyebrows, and wait for their move. If you're both suddenly doing the challenge, work together to stay within budget.
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The Cheapskate Backhand
When dealing with someone cheap, never suggest activities where you'll end up paying. Only agree to free bullshit like yoga in the park. Never forget, when you're running these cons, it's best to conveniently "leave your wallet at home." If Mr. Never-Has-Funds wants to make a detour for coffee, he'll have to pay for it himself.
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The Reach Around
Have some drinks before you go out and make sure you have a good buzz. When your friend walks off to use the bathroom, drink their drink. This can be done with coffee, food, or booze. Congrats, you're now the cheapest person you know.
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The Don Draper
Cut your losses and stop hanging out with them altogether. Avoid places you'll be sure to see them. Change your name. Move to a different city. Start a whole new life.
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The Hammer
And if none of that works, cut the foreplay. Tell your penny-pinching cohort you're done paying their way. Don't make a big production out of it. Tell them simply, kindly, and firmly that you're done dealing with their tightfisted ways. Prepare for them to feel hurt and rejected because honestly, the only people who do this are kind of a dick.
