Real talk: I have very little experience in traveling alone. Part of the "problem" is that I have friends in a lot of different states, so "I'm coming to your area, want to get together" ends in them either inviting me to stay, or us going "Do you want to do this thing and that thing and also this other thing together?" and then I can't say I did it alone. Maybe one of these days I'll say I'm doing research for my blog and pick somewhere random and cheap to go alone, just for the experience.
Also real talk: I haven't flown with anyone since I flew from LA to Chicago with my mom in 1999. I'll go on trips with people, but it's usually involved me meeting them there. I have a System, and when I have to fly with someone later this year I have no idea how I will handle it. Which is part of the reason for this post.
I've yet to have a bad experience going on a trip with someone, which is part luck, and part me having awesome people around. I've heard horror stories from others. They'd go on a trip with someone and the other person would be in such a bad mood that it ruined the trip, or everything went wrong and they couldn't bounce back from it, things like that. And hey, things can and will go wrong. Holy hell will you hear about things going wrong when I get to talking about my most recent move, and when I tell people about it they assume it was a terrible trip. It wasn't, and a lot of that is because I made the trip with Nick. He and I have a solid system, and a lifetime of knowing each other means we know when the other one is getting too stressed and they should just leave something alone, and we can almost always laugh the bad things off in time. It's the bonus to having a sibling you can get along with for extended amounts of time. My Chicago to LA trip was stressful sometimes, because I was moving and it was sad and stressful and there were times when we all weren't jiving right, but I also can't say it's a bad trip.
You can't always guarantee that you have a good travel buddy. It's like any other relationship you choose to be in, really: you need someone you can get along with, that you can handle problems with. For the time you're on the trip, it's you guys together, and the problems that pop up are things you're going to have to deal with together. If you're going with a friend who can annoy you, it might not suck to make sure it's a shorter trip, or to build in something where you can get a break from each other if you need it. "I need to get coffee, want anything?" and then fake that there was a long line at the hotel Starbucks or whatever if you need to. I've got a friend that I love like crazy, but she and I are just similar enough that when one of us gets annoyed we set each other off and then we're both annoyed, so we take time off from each other or try to hang out in larger groups. You don't need to do everything together. In fact, feeling like you can change your plan and/or aren't shoehorned into doing everything together or everything the other person wants to do can help a lot. It's a bit harder if you're trapped in a small space like a car together for a long time, but then you might want to bring some icebreakers along: books on tape, comedy podcasts, a playlist of songs you can dance it out to or play too loudly to talk over.
Compromise is key. If you can get along the whole time and you have all the same interests, that's great. But just in case, be prepared to give up on something here and there. If one person really wants to do something that the other doesn't, see if it can be less than a whole day thing. Alternately, if say you get to listen to something the other person hates for a while, let them choose the next thing you play. Try to make it as much of a 50/50 split as you can (or 33.3%, or 1/4, or however many of you there are), so no one's taking over and no one's slinking into the background. Let me put it simply: everyone should just try not to be a douchebag. Remember that trips can be stressful, and everyone can get tired and annoyed (and annoying), and if you're feeling it, your travel buddies probably can too. And hey, if you have a terrible time and you know you can't travel with someone, there's no shame in not going with them again. Or in suggesting that you bring other people along to make it easier on yourself.
And you know what's awesome? When you get surprised. I had a friend visit me in LA and I was a little nervous at how we'd get along for days alone together, because of that group she's probably the one I knew the least. And as it turns out, we have very similar interests and think the same way when it comes to this stuff, so we're both easygoing but can still come to a decision on what to do. So now when I think of a trip she's one of the people I want to convince to go with me, because I know we can handle it.
Come to think of it I think a goal in life might be to amass a whole group of people I can travel with always. As goals go, I think it's a great one. I am going to get right on that.
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