Project Crew/Entourage

An issue that I have seen for years now is: planning events for a group. This can be as simple as organizing a dinner for later on the night. But as you probably know, it's not as simple as just choosing a place and meeting there. There are various steps you must go there to achieve (Sometimes)
In terms of organizing dinner, you must find the types of restaurants would eat at, while taking considerations of individual cravings. Then, particular people desire to try something new (some don't), the beer selections, price, and atmosphere. After you take those into account (If this is done by SMS, you have taken about 2 hours to get to this step), you'll be left with no choices, usually. So someone will have to make an executive decision, resulting in heartbreak of some. You have to be starved or a strong-willed person to be this person. And once time comes for the dinner, getting the correct number of people will actually come is impossible (Remembering who was asked/responded is impossible). You never want to be the first person there! Especially if you didn't plan it!
And after dinner, there's the awkward moment(s) where you leave the restaurant. If it's a weeknight, it's usually simple, and people will assume home is the next destination. But some people have difficulties ending a conversation or just don't know how to end the night. As a result, it's odd feeling of people wanting to go but it's really just people having small conversation just standing around. If it's a weekend night, it's even more difficult. At the end of dinner, planning for the after-dinner events takes place at the table or just standing around outside the restaurant.
The most common question, "What do you guys want to do?" (This will be asked multiple times). The most significant issue with this question is everyone probably wants to do something different. There will be some that will want to go home (Lame), some will want to watch a game or something, some will want to drink quietly, some will want to do something active (Dancing!), and some will want to try something new but have no suggestions. People will always have different goals for the night. At the end of the night, the most aggressive/vocal person(s) will get it their way.
So this is the problem I will be working on. I will reflect/discuss this issue occasionally on this blog. But how can this problem be solved, that is: How can planning events for a group of people be made easier?
Comments/suggestions are encouraged!