Dear Reverend,
Every time I go out to eat with my friends, I wind up being the one who figures out the bill. I often just pay the whole thing and collect money after. Most people have Venmo, so it’s a lot easier than it used to be, but there’s always at least one person whom I have to hound to pay me back. I absolutely hate having to ask people for money, so how can I quit being my friend group’s treasurer?
V. Saugh, (man, 51)
Dear V. Saugh,
The simplest way to solve your problem is to start asking for separate checks. Some restaurants have restrictions on splitting checks for very large parties, but if you’re polite about it, most places will accommodate however you want to pay. You just need to let your server know at the start of the meal, not the end, so that they can keep track of who orders what. Easy-peasy.
If you find yourself picking up the entire check again, make sure everyone settles up before leaving the table. Of course, you should be mindful of how busy the restaurant is, but the accounting shouldn’t take too much time.
An easy way to handle a slowpoke on Venmo is to send a request for the amount they owe. There’s even a “remind” button built into the app that you can use if they don’t respond to the original request right away. For a more direct approach, text the group something like, “That was a fun dinner. Bob, please send me $38 when you have a sec.” I hate to say it, but a little public shaming goes a long way.
There’s no need to feel weird about asking for money that you’re owed. If you’re good enough friends to be sharing a meal together, you should be able to talk about how to pay for that meal.
Good luck and God bless,
The Reverend
This article appears in Money & Retirement Issue • 2026.
