Re: Terrible at group dynamics
Why did you invite the friend to begin with?
This is simple enough. You should still go on the road trip. Backing out now will make you look like a chump who doesn't go through with his plans, or even worse, someone who starts whining when he doesn't get his way. Right now I'm throwing you in the latter category, so I think we should change that.
Instead, what you need to do is take control of the situation. This is a classic case of needing to AMOG the shit out of this guy, so here's what I suggest.
Go grab drinks with everyone. This is important, because in order to take some power from this guy you need the social proof. When you get to the bar, grab the first round for everyone. This way there's this implicit idea that you're not a cheap ass and he can't call you out for it. Next, you're going to want to sit down with everyone and do one of two things: (1) make it very clear that everyone should chip in for the rooms; or (2) recommend that you and the roommate grab your own rooms and the friend and the guy grab their own room. I decided to give two suggestions here simply because I don't know your economic situation, but I think option 2 is better for all the obvious reasons.
As far as making plans go, this is where you want to AMOG this guy all the way to the other side of the planet. What you're going to need to do is let him talk. Get him to tell everyone his plans, but then lay down what you ARE doing. Make sure you compromise a couple little things that he wants so that it appears you're listening to them. Here's how your side of the conversation should look:
Him: Rambling on about whatever the fuck he thinks you should do.
You: "I really like X idea. That sounds like it will be awesome. So here's what we do..."
You're not asking if they think that's what you guys should do. You're not supplicating to him. You're being a reasonable guy who is taking control of the situation and making a plan. The women love it.
The other guy might get all bitchy about the situation if you do this. In that case, you have to make everyone believe you're listening to his suggestions and then give random ass reasons why they aren't good ideas. He'll get pissed but everyone else will eat it up as long as you give off the appearance of being fair.
If he won't drop it, start talking to him like he's an inferior. What I mean by this is start using the voice you'd use if you're talking to a child or a handicap person. Use inflection and whatnot to show that you're concerned for him, but you're not taking his ideas seriously. The key here is to sound as sincere as possible.
Do this and see where it gets you and come back and let us know. Also, if you're having drinks with the roommate in a few days, try and get a sense of what she's feeling about the plans, but don't whine, complain, or bitch about this other guy.
Honestly dude, right now you just sound like a kid who isn't getting his way and wants to take his ball and go home. We can turn that around though
"It's only after we've lost everything that we're free to do anything."