When you bring someone to a restaurant in Russia

Will the man order for both or will the parties order individually?

If it is a romantic/dating encounter, the man and woman confer over their choices and each makes their own selection, but then the man does the talking. The man will select the wine and propose the selection to the woman.

If it is a business encounter each person talks individually to the waiter. The person who invited will select the wine. For the main course, guest can ask the person who invited something like "...all of this looks wonderful, what do you recommend?..." Generally the person who invited will know the restaurant and make a good recommendation.

Language barriers can influence how this works, my experience is mostly where both people speak Russian. You can also ask for English menus but invariably the waiter will spot a foreigner when they arrive and offer English menus when you are seated. There are English menus even in remote locales, but you can always call ahead to make sure. But if one person does not speak Russian, then the other person does the talking.

In the "classic" scenario, the woman is Russian and the man is western with no knowledge of Russian. They met on a dating site and the man is now making an exploratory visit. The woman already knows which restaurant she wants and will do all the talking. If you are observant, you'll spot her friends at another table just drinking water or maybe sharing a glass of wine; they are checking the man out (plus everybody in the restaurant can tell what's going down, especially if the woman does not speak English and they have no common language). The man pays (by credit card) and tips according to his own tradition.

Do you tip the waiter/waitress at a restaurant and how much?

For me it depends upon the location, in Peter and Moscow I follow the American tradition and add 15% to the credit card tab and may leave a few rubles in cash but never less than 400 - 500. For inland locales like Perm or Tomsk I will use the European tradition and leave less, maybe 7% - 10%. The last time I was there was June in Stavropol and I had no rubles and only about 20 pounds in Sterling and about 30 Euro. I tipped on the credit card 10% and left a fiver in Sterling and that was gratefully received. But honestly, it's a matter of personal choice.

In another scenario, I am on commission as a translator or guardian/nanny and of course do all the talking. The client pays but consults with me over the tip.

Generally, in case of dating a man pays for both, but each one orders on their own. Tip depends on the person. Some people pay, others do not. Tip may be from 50 rubles (1$) to ... any amount :) 100-200 rubles on the average. You can just leave the change.

For paying in a restaurant, this really does depend. In case of dating, usualy a guy pays for both, but on early stages or in special circumstances it can be any way. In other cases, e.g. a birthday party in a restaurant, usually everybody pays for himself. In case of some business evening (dining with a business partner), it also can be really different. When a big company eats out and orders together, usually at the end everybody would estimate how much they have to pay, and give approximately that amount to one person, who then goes and pays for all from these collected money.

As for tipping, my approach is to leave approximately 10% of bill, plus-minus 5% depending on how much I liked the service. This applies only to places where a waiter comes to your table and serves you; for a cheaper cafes where you go with a tray, take some meals, pay and then go to eat, no tipping is usual.