I'll add my 2 cents. I do live in the greater NY area, and I can't recall ever being asked by the waiter, in restaurants here, if we want the check separated.
The vast majorty of the time, we just split the check.
Out to lunch with a girlfriend, no question, it is always 50/50.
Out to dinner with close friends, even if someone has a drink or two and the other couple doesn't, 50/50..unless someone orders like 10 drinks and we've had none (or vice versa) and then it's always the person who ordered more who insists on looking at the check and paying what they owe.
The other night my husband and I went out with 2 other couples to a local pub. We had no alcohol at all, the other 4 people had a bunch. We didn't ask for separate checks, but when it came it wasn't just split. Ours was easy, 2 entrees, 2 sodas, I added it up and we threw in our total plus 30% to cover tax (7%) and tip.
The other 2 couples looked at the bill and figured out who got what, I wasn't really paying attention. After everyone had paid, I said, we're good? to the last person to put cash in, and he said Yes. If he had said no, we would have thrown a couple more dollars in, even though I knew we had paid ours + extra, but I wouldn't quibble over a couple of bucks. I think our portion was $35 someone else's was $75 and I didn't hear what the 3rd couples was, but close to the $75 of the second couple, so it was a marked difference.
2 weeks ago, 3 girlfriends and I went out to eat and ended up with 3 pitchers of margaritas. One of the girls was the designated driver so she had a small glass of margarita at the beginning of the meal and that was it.
At the end of the night, the 3 of us who drank decided since we had $80 of margaritas on the bill it would be easier to treat our non drinking friend to dinner and we split the bill by 3 and paid with 3 separate credit cards-people do that ALL the time here, it's not even blinked at by the server.
The other friend insisted on leaving the tip.
On vacation in SC this summer, waiters often asked if we wanted separate checks, and I usually said yes.
We were with my brother and SIL for every meal and they have no kids, we have 2. I'm not making them split 50/50 when they are 1/3 of the group, and if the server is going to offer without me asking for separate checks, I'll take advantage of not having to do any math at the end of the meal.
One night we went out to eat without the kids and we just split that 50/50 regardless of what anyone ordered.
Once we had separate checks because we had the kids with us and my brother's app ended up on our bill. He tried to give us money for it and I refused.
It's not about nickle and diming, it's about making it easy. The splitting 50/50 I don't care about if I am the one who ordered less, I DO care about paying my full share when I am the one who ordered way more, so it's not about being cheap, it's abotu making sure no one is paying extra for me.
Oh! Japanese steakhouses where you sit at the grill with strangers, they will ask if you want separate checks and since they do that there all the time for the same table, we say yes, again, just to make it easier, no math to do at the end of the meal, other than adding 20% for the tip.
In conclusion
in this area, I would not ask for separate checks because it's not something I think about, nor is it offered
BUT when offered, if we are an uneven group(we have kids, or more kids than the people we're with) then I say yes.
Depending on what was ordered, sometimes we look at the bill and pay for what we ordered, most of the time with an equal number in the party, we just split it.
I never feel that any of the ways of going about it are awkward.
