Choosing a Date, Time, and Place
When you decide on the spur of the moment to grab a meal or a drink at some casual restaurant or bar- a laid-back place, where you know there'll be room for everyone to squeeze in- it's fine to simply whip out the cell phone and invite whoever you think might be interested. In this sort of informal situation, if the other person makes it, fine; if not- well, that's fine too. In fact, casualness is one of the nice aspects of impromptu get-togethers.
If, on the other hand, you have a desire to sit down with some friends in a nice restaurant to enjoy good food, good drink, and good conversation, your natural spontaneity is going to have to give way to some planning. This means picking a specific time and place well ahead of time, pinning down who will be attending, and confirming your plans with your fellow diners once everything is set. If the restaurant where you're planning to eat is a happening one, you may also need to make a reservation ahead of time.
Scheduling a dinner at least a few days in advance makes it easier to select a time and date that works for everybody, and it also sets the night apart as something special- a date to be looked forward to with anticipation by all parties. Unless you're hosting a meal to celebrate someone's birthday or other milestone (in which case the schedule of the honoree takes precedence) setting the date and time is really a matter of finding a slot that works for everyone. The best way to accomplish this is to call or e-mail the people you're planning to dine with a week or two ahead of time, and offer them several possible dates. Feel free to indicate your own preference if you have one.
Picking the place also takes a bit of forethought. You'll want to choose a restaurant that everyone is happy with. You may have a spot you're dying to check out- and if so, it's fine to say so. At the same time, you need to be sensitive to other people's likes and dislikes, as well as any special dietary requirements they might have.
If you plan to pay for the meal of the person you're inviting, then the time to make that clear is when you're first extending your dinner invitation.
Happy Birthday! Got any cash?
If you’re organizing a special occasion out at a restaurant or bar to celebrate a friend’s birthday or other life or career milestone, you can’t expect your friend to pay her own way. It’s the group’s responsibility to split the honoree’s tab among them. On the other hand, it’s not okay to invite a bunch of friends out to dinner to celebrate your own birthday, and then expect them to chip in for you. If you’re the one who suggested the dinner, it’s incumbent upon you to offer to pay for your own meal.