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LPT: Always carry enough cash for just yourself when eating out with others, especially if you don't know them that well
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In college and during my post-grad life, I would often front the bill when eating out with acquaintances or my friend group. The expectation would be that people Venmo'ed me what they owe after.

With acquaintances, there's a risk of not getting paid back since I don't know them that well.

With my friend group, although they paid me back, it would sometimes take days, reminders, etc. I became known as the "transactional" one in the friend group because I was always asking them to Venmo me. My friends would jokingly say "I can't believe you're actually making me pay you back", or "No F--- you" (as a "joke") when I ask them to pay me back. If you're always the one asking your friends to pay you back, I think at least subconsciously your friends will start to think "why is ____ always asking me to pay them?"

I think separate checks is obviously the best option, but some places don't split. Plus, it can be hard on the server if there's more than 2 people. There's also the option of asking people to Venmo you back right away (at the restaurant), but that can be a little awkward too (or their phone died, has no service, etc.). It can also be awkward to calculate how much people owe you right at the restaurant.

By carrying cash, you can put enough cash on the table for just what you ordered, tax, and tip. If asked, just say the rest of your cash is needed for later, and your credit card doesn't work. The rest of the bill is not your problem. If someone else puts their card down, they can take the cash you put down. Or just let the rest of the group put down as much cash as they owe.

Disclaimer: I know a lot of friends proactively pay back what they owe. This tip is mainly for when you go to dinner with people you don't know well, or your friends are bad with paying you back.

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8 months ago