Dear Friend or Foe,
Since we were kids, my friend—"Dana"—has been chronically late. Over the years, my close-knit circle and I have learned to order at restaurants without her and never to depend on her to fetch us if we're stranded somewhere. We've put up with the behavior because she's always been there for us emotionally. She's also a lot of fun when she does eventually show up. Since we graduated from college a few years ago, however, the problem has gotten out of hand. There's always another excuse—e.g., she just painted her nails and doesn't want to drive.
I live in a different city than the others now. A few months ago, I took the train to their city and we were all supposed to meet for coffee, then move on to dinner at a location to be decided. Half an hour after the appointed meet-up time, Dana texted to say she wasn't coming because she needed a nap after work, but she'd come for dinner and to let her know once we'd decided on a location. She then decided she didn't like the restaurant we chose and asked that the three of us come to her instead.
It hurt that Dana wouldn't come out over the choice of a restaurant. (Though she made it to the other events we'd organized for the weekend—and acted as if nothing happened.) But I've learned not to take it personally; she does this to all of her friends. I roomed with her for a year in college and she was late to every class. More recently, she was upset that a co-worker stopped carpooling with her after she made him late to work every day. My friends and I have tried to talk to her about this, but she just laughs it off and says that's just the way she is. My friends and I love Dana. But how do we get her to see that people who are "just like her" ultimately find themselves without friends like us?
Finally Fed Up
You don't say if, at Dana's insistence, you agreed to cancel your restaurant plans that night or not. But in terms of teaching Dana a lesson, refusing to accommodate her selfish whims would be a good place to start. For that matter, if I were you, I certainly wouldn't have gone out of my way to keep Dana abreast of the weekend itinerary after she'd already sabotaged Friday night. (She needs a nap? Find me someone who doesn't!) People like Dana need to recognize that if they hold up every train, eventually they're not going to be invited to get onboard.
It seems to me that you and your friends—at least until now—have been far too forgiving of Dana, indulgent, even. Next time you make plans to come visit, I'd go so far as to leave Dana off the list of dinner invitees. If she finds out and protests, tell her that last time you came to town she didn't seem to want to make the effort to come out. So you just figured you'd "leave her alone" this time. Maybe she'll start to get the message.
A shrink once told me that chronic lateness is an aggressive act. It might be passive-aggressive, but it's no less maddening (and hurtful) for the people who are standing there twiddling their thumbs. Why? It sends the message, intended or not, that the Late Party considers both you and your time to be essentially worthless.