Prose and cons
The obvious solution here, of course, is to go back to the age-old standby of text stories. You write up how the interaction went, post it in a forum where everyone who cares can see it, and then just move on. Clean and simple, right? Except for the fact that no one will read it.
OK, I lied. Some people will read it. But not everyone will read it. As bizarre as it might sound, there are people for whom roleplaying is an alternative to reading. (No, I don't understand how reading lines of chat text is different from reading a prose story.) No matter how good your writing might be, there are going to be players -- some of whom really deserve to be involved in this meeting -- who would rather not read a straight text recap.
And there might very well be other players involved, too. If Alice and Claire are going to exchange words, Bob's player probably wants to be there. Desmond, Edward, and Felicia's players might want to be involved with this as well. Suddenly you're going to have to take control of an awful lot of other people, putting words in their mouths, assigning motives, and possibly creating some long-term consequences that everyone will have to deal with. And no one except you had control over any of that.
Plus... well, let's face it. There are good roleplayers who are not good writers. The skills are similar but not identical. Roleplaying teaches dialogue and characterization, but you can skate by without being good at plot or pacing or descriptions or a lot of other things. I know, I know, you're great, but you have to think of all the people who aren't so great.
This isn't to say that a text story can't work. It's just to say that it might not be your best plan to begin with.
The other Darren
As often happens, the best option is in games that let you cheat. Like Guild Wars.
See, Guild Wars identifies characters by first and last name. So Alice would more properly be Alice Abernathy, Bob would be Bob Baldur, and so forth. This means that in theory, there could be a Claire Caterwaul, a Claire Catterwaul, a Claire Caterwall, and so forth. You see where we're going with this.
If you have a fellow roleplayer willing to, essentially, opt out of playing his or her normal character for an evening and step into the shoes of the alt in question, you can have the scene go down more or less normally in the game. Sure, Claire-2 might not quite have the same equipment as Claire-Prime, and she might act just a touch off, but assuming the person filling in is familiar with Claire, the approximation is close enough to keep the scene moving briskly.
Of course, all of this necessitates a lot of conditionals. You need a trustworthy friend to play one of your characters and want to be involved in the scene while having no problem with the fact that his or her own character is not a part of that scene. And that's assuming that said friend has a spot for an alt and that the scene will take place where Claire-2 can actually travel.
Also, not every game lets you get away with Claire Caterwaul and Claire Caterwaull. In a large enough game with single names, the odds are not bad that most variants on Claire are taken, and it becomes harder and harder to ignore the fact that everyone knows it's not actually your alt right there. A few breaks from reality work out OK; too many and it's less a scene between two characters you play and more like a scene between Norman Bates and his mother.
As I think I've established by this point, I'm a big fan of taking roleplaying beyond the game client. I'm written long in-character letters to people that were sent via email, I've kept character journals, I've even tried to scrawl out some of my character's handwriting for future reference. So it's no surprise that one of my solutions for dealing with a meeting between characters that can't meet in-game is to take the scene out of the game. But not via raw text -- via chat.
Seriously, the web is just plain sick with chat clients. IRC and AIM are my usual weapons of choice, but even Ventrilo has a chat client. And while all of these might require a bit of workaround, the fact remains that in each of these cases, you can set up multiple profiles and access them all from the same computer.
The obvious downside, of course, is that many players would rather have a roleplaying scene in-game instead of having to download and install a new chat client. But the advantages should be obvious. You'll be the puppeteer for both of your characters, and with a few exceptions, most of the things you would be doing in the game would largely be expressed via lines of chat. Unfortunately, you would still wind up missing out on the visual aid that the game provides, which would likely make things feel a bit more sterile even if the actual scene played out wonderfully.
None of these is an ideal solution, of course. But I seem to be taking on a lot of problems with unclear solutions lately. And if you really need two of your characters to meet, you can't just pretend it's not an issue forever. Sooner or later, you need to get them in a room and let the sparks fly. Even if that room isn't in the game proper.
Feedback is welcome in the comments or via mail to firstname.lastname@example.org. You know, like I say every week. Next time around, let's take a look at the right time to take a plunge, starting with a story about death.
Every Friday, Eliot Lefebvre fills a column up with excellent advice on investing money, writing award-winning novels, and being elected to public office. Then he removes all of that, and you're left with Storyboard, which focuses on roleplaying in MMOs. It won't help you get elected, but it will help you pretend you did.