When traveling with someone you get a sense for what a person is like in that you get to see what they do at times when you wouldn't normally be observing them- when they're alone and have unstructured time. If you live with someone you probably get a representative sample if you happen to notice what they're doing when you return from having left them alone, but you never know everything for sure. It's hard to keep secrets in a hotel room.
This is yet one more reason to be truthful in your relationships. Not that you're going to end up traveling with everyone you're close to, but you can rest assured that most anything you've been trying to hide is going to get found out if you spend 3 weeks in a hotel, of if I go back to some close college friendships, 5 or 7 weeks in a car with someone.
Oh, and good luck hiding stuff from yourself too. That's, to me anyway, one of the great values in traveling alone for an extended period. You get to see yourself in a variety of situations, great and awful, routine and spectacular, and see what you do. Are you brave? Cautious? Opportunistic? Flexible? Are you good at planning, improvising and enduring? Forget about college applications, this is when you find out what your strengths and weaknesses really are.
I'll throw some old stories at you a bit further down the road, but here are a few pictures from the trip to date:
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