By Rob Pegoraro
Thursday, July 10, 2008; D03

A lot of Internet users now find they have two kinds of address books: Ones they've known for years, and ones that are up to date.

The first kind lives among programs people have run for years, most often Microsoft Outlook or Apple's Address Book. These are always available, Internet connection or not, and can be synchronized with a phone or handheld organizer.

But the only way to update them is to sit in front of the computer and start typing.

The second kind resides in social networking Web sites such as Facebook and LinkedIn, where friends, family members and business contacts post their latest coordinates alongside updates about work and social lives. This address book is always up to date -- but it remains confined to your Web browser unless you copy and paste each new phone number or job title from an online profile to a contact-list program.

Ctrl-C, Alt-Tab, Ctrl-V (on a Mac, Cmd-C, Cmd-Tab, Cmd-V), repeat as needed: It's one of the more mind-numbing forms of digital bookkeeping around, up there with reconciling bank statements in Quicken or Microsoft Money.

Why can't our address-book programs learn from our social networks? The latter are all too happy to sponge off the former, inviting us to upload contact files so they can find our friends. But if you try to reverse the flow of data, the sites may not be so generous. LinkedIn lets you download a "Vcard" contact-data file for one user at a time, and Facebook doesn't even permit that.

It's not as if cooperation is impossible. For years, the Plaxo address-book service Comcast just bought has allowed continuous updates from Web to program and vice versa. But far fewer people use Plaxo than visit the social-networking hubs.

Those networks are finally catching up -- but in a slow and bureaucratic manner. Facebook, LinkedIn and some other sites now allow a handful of third parties to extract their users' data and use it elsewhere.

These initiatives could lead to the ideal address book that updates itself -- no more bounced e-mail messages, no more returned-to-sender greeting cards.

For now, though, the best you can get is a free plug-in for Outlook called Xobni ( http://xobni.com), pronounced ZOB-knee. In addition to its core job of analyzing e-mail archives to piece together the patterns of your social network, Xobni -- "inbox" spelled backward -- two weeks ago added the ability to connect to LinkedIn. Install this software and a sender's public data (employer, title and photo) will appear in the Xobni sidebar.

This can be neat, but it could be much more useful. LinkedIn public profiles only contain the most basic info, while the private profiles of people in your own LinkedIn network provide a résumé's worth of data.

Xobni also won't update your Outlook contact list with the info it fetches; once again, you must resort to the old Ctrl-C, Ctrl-V drill.

LinkedIn and Xobni both say they are working to enable that sort of deeper connection, starting with access to private profiles. Facebook, meanwhile, says its Facebook Connect framework should allow the same type of interaction -- although Connect, announced in May, lags behind LinkedIn's efforts, launched last June.

Both LinkedIn and Facebook, however, are carefully screening the companies using these new programming frameworks, evaluating how much access they seek and how their users might employ it.

They face real risks: What if a spammer uses these features to harvest contact information? What if a rival network does the same? But they also risk going too far trying to manage these risks.

The stickiest situations may arise from attempts to enforce their own privacy rules. Consider what Facebook says it wants to do -- ensure that a user's privacy settings follow the data going outside Facebook's network. This "dynamic privacy" concept could result in such odd situations as a friend's data vanishing from your computer's address book when he decides he never liked you all that much.

LinkedIn shares similar goals. "On LinkedIn, each person owns their profile and must maintain control over it at all times," e-mailed Lucian Beebe, the site's director of product management.

When that kind of remote control comes attached to music downloads, it does so by the name of "digital rights management" and annoys listeners who find that a song won't play anymore. Are people ready for DRM in their address books?

"Interoperability" -- getting different tools to work together -- is one of the hardest tasks in the business. Think of the Bluetooth phone that won't talk to your Bluetooth-enabled laptop, or the gyrations needed to move an archive of e-mail messages from one mail program to a competing application. Getting social network sites and address-book software on speaking terms won't be any easier.

But it has to happen here: The C and V keys on my keyboard are starting to wear out.

Living with technology, or trying to? E-mail Rob Pegoraro atrobp@washpost.com. Read more athttp://blog.washingtonpost.com/fasterforward/