Pre-fix menu. Ask people to PayPal you in advance whatever plate price is + estimate 1.5 beverage each + tip. And if there's a shortage, you cover it yourself. I've never done this but this is how I'd probably do it.

Why can’t grown adults figure out how much they owe? WTF

Does the restaurant know at least 22 people are going to descend upon it at once? Most places would not be able to seat you without a reservation, and would insist upon a fixed menu. Do not just roll up on them unannounced—you’ll be turned away.

OP here. Thank you all for your advice. My sibling and I spoke about several options posted here, and decided we are just going to split the entire bill. We figure it'll be around $1500, possibly up to $2,000 at the most including tax and tip.

Not per family, but per table if you don’t get a private room. What kind of family is it that 4-5 people can throw their cards down and be done with it? Not all computers make separating checks easy.

Anonymous wrote:Ask the restaurant for a fixed price menu.

If you can't get a private room, go this way. Send the menu out with a reminder that for that size, the restaurant is adding an automatic 20%gratuity. Once person should pay and the others venmo. Keep in mind that it's not going to come out even steven and the whole point is to spend time together, not quibble about pennies.

Go to a place with a fixed-price menu or get a private room where they can do a set price for everyone (drinks could be extra and by family).

Anonymous wrote:One person pays the bill. Still divvy it up however necessary ($X for the family of 5, $X for this couple, $X for this single person, etc), but Venmo the amount (including min 20% tip) to the bill-payer. Much easier on the restaurant.

No, don't do this as one person could spend $20 and another $200. Not everyone may be able to afford more than what they ordered.

Each person pays their own bill.

Ask the restaurant for a fixed price menu.

Anonymous wrote:

Anonymous wrote:A bunch of extended family/friends are getting together for a restaurant dinner. So far it's 22 people, ranging in size from 1 person to five people. How do you suggest we split this bill?

I would ask for separate checks for my family.

+1

It’s not a big deal.

Anonymous wrote:

Anonymous wrote:You let the waiter/waitress know that there will be a lot of separate bills and then as they take orders they note who is paying for what.

OMG, no.

Actually, we had a large group and the waiter suggested we order this way.

^ above. Discuss ahead of time with whomever in the family will get the bill so they can decide if/how they are going to collect from their other family members.

Anonymous wrote:Separate checks per family.

Just make sure they all sit near each other. It's murder for a server to have to keep track of "I'm paying for me, the blond girl at the end of the table, the young boy at that table over there and half of the bill for the old couple."

Honestly, I would pay the bill myself and get Venmos from everyone. Lots of points!

Separate checks per family.

Anonymous wrote:A bunch of extended family/friends are getting together for a restaurant dinner. So far it's 22 people, ranging in size from 1 person to five people. How do you suggest we split this bill?

I would ask for separate checks for my family.