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Maybe it's generational. I'm not always on time, but I feel guilty if I'm going to be even 10 minutes late, and apologize profusely. Most of my friends feel the same way.
One way to cope is to not let them make you wait. If you agree to meet at a restaurant and they're not there, start without them after a reasonable time. If you're supposed to meet at a theater, make sure they know which one and which show. And if they're not there a few minutes in advance, go in. They know where you're supposed to be. And _do not_ buy their tickets for them.
Just be positive about what you intend to do. Say, "We'll meet you at thus and so place; and if you're not there, we're going on from there to thus-and-so, and you can catch up with us there." They will, or they won't. But it's no longer you trying to make it all hang together. You've put the responsibility back on them, where it belongs.
In fairness, when making arrangements with people you like who you know have tardiness problems, you should check to make sure that they're thinking realistically. If they say, "fine, I can meet you there at eight," double-check: "Are you sure? You sure you can get there from work that quickly?" "Well, maybe not...." And maybe they'll give you a more realistic estimate of when they'll be there.
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