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Comment by JumpCrisscross | Hacker News Reader

When I spend more at dinner, I eyeball the cheque and ask for a little more to be put on my card. If we're alternating between who picks up the tab, I'm mindful about buying them drinks. Venmo just makes cash-only, "no more than 2 cards" dining and vacation booking easier.

Note that I've had friends try to split bills to the penny. I tell them to stop, because both our times are worth more than that. (The exception being if I know they need the extra cents, in which case it still seems more reasonable to round down in their favour.) That kind of gentle social shaming is productive and something I've noticed a lot of people my age shy away from.

TL; DR If you think Venmo is ruining your friendships, it probably isn't Venmo.

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Addendum: One useful thing I've found about reimbursing (note: NOT splitting, which is what you were talking about) some other bills down to the penny is that it makes it much easier to search for them afterward if you want to figure out whether you remembered to pay for them. Like if you buy someone dinner and they insist on paying, don't round $10.49 down to $10 or up to $11. Because then you have different numbers showing up on different accounts (credit card statement vs. bank statement vs. Venmo/whatever) and it makes it harder to see if you remembered to pay for it or not.

Aside from the social awkwardness/pettiness, it doesn't really work for typical bill splitting anyway, since it's not like they would remember what amount to search for, given that usually the person paying has the only receipt. Where this method really shines is when someone is reimbursing you in a bulk/lump payment -- in that case it's far more valuable to know that the actual amount was $304.01 instead of just something rounded to $300, since then it'll be a lot more work to figure out if that payment included a $6.23 item or another $7.98 item or whatever.

If you like this, you might like the free workshops from You Need a Budget. I like to think of it as teaching "poor person's double entry accounting". (The workshop is free because they're trying to sell you their $50/year SaaS.)

https://www.youneedabudget.com/classes/

It's not really about budgeting or tracking your expenses, rather it's about (1) making it easier to search for the exact amount and having the payment pop up (e.g. in one shot in your email inbox, in some cases) when others ask you if they paid, and (2) avoiding a misunderstanding where someone asks you if they reimbursed you for something a few weeks later and you say "no" because the amount you looked for didn't match what they actually paid you.

If you end up with a running tally of bills (either splitting or alternating or what have you), I'd recommend SplitWise to keep track of who owes what to whom. It also has a simplify debts feature so that if you owe X to a friend and a friend owes Y to you (where X>Y), the friend who owes you can just pay the friend whom you owe directly. It also works great for rent, utilities, pizza, etc. in a room mate situation which is mentioned in the original article.

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