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Facebook is about to turn eight years old, and it looks like the social network has some awkward years ahead of it. As the young company is starting to do thing grown-up companies do like form a political action committee to get cozier with Washington, Facebook is having a hard time shedding some of the baggage from its youth. The excitement of Facebook's unveiling of Timeline and new class of social apps last week was quickly dashed by familiar privacy concerns. This week a wave of speculation about why Facebook's iPad app hasn't launched yet left many to wonder why the company looks so disorganized. Inevitably, the growing pains are signs that Facebook is entering a new phase of life, and the transition won't be easy.

Some of Facebook's new grown up problems are familiar ones like outrage over privacy concerns and the user revolt that every new feature refresh spawns. Mark Zuckerberg couched the announcement of the new profile design and app platform in language about how Facebook is making it easier to share your life with friends. However, as tech bloggers quickly pointed out, this means that Facebook will also be sharing more of your personal information with third parties. Following the announcement of Facebook's new features Dave Winer worried publicly that Facebook was was scaring him by not only inviting people to share more but also "seeking out information to report about you." He suggested that users log out of Facebook to protect their private data, but developer Nik Cubrilovic blogged the following day about how even when you logged out of Facebook, the social network's cookies continued to track your activity online. In fact, Facebook has been doing this for over a year.

Facebook has defended itself against the cookie claims, but the confusion about the site's new features is a symptom of a bigger communication problem. To continue the awkward youth metaphor, Facebook's voice is cracking a bit, and at times, it sounds too sure of itself. New information about the company's awkward dealings with Apple show that the company is struggling to form difficult partnerships but also frightening off employees in the process. Nick Bilton at The New York Times reports on a Facebook employee who fled to Google after Facebook failed to launch its fully built iPad app due to difficulties negotiating with Apple:

Although Apple and Facebook have successfully worked closely together on a number of products, including the Facebook iPhone application, the two companies have also had a strained relationship.

This connection began to sour last year when Apple moved into social networking with the iTunes music network Ping. At the time, Facebook was curiously missing from the product. Steven P. Jobs, Apple's chief executive, said that Apple had been in discussions with Facebook to integrate the social networks, but in the end, Mr. Jobs reportedly said Facebook's terms were "onerous."

Mashable says that the social network's new mobile apps will be included in Apple's expected announcement of the iPhone 5 in October, but the disagreement between Jobs and Facebook has already led to Apple forging a closer partnership with Twitter.

As the drama has been playing out in Silicon Valley, Facebook has been working hard to build closer relationships in Washington. In addition to forming a PAC, Facebook is embarking on a partnership with the U.S. Chamber of Commerce to offer free advertising to small businesses, a goodwill gesture that comes just a few days after Google's former CEO Eric Schmidt defended the search giant against antitrust accusations on Capitol Hill. If Facebook is the awkward adolescent tech company, Google is the big brother who's gone off to college and gotten in some trouble on campus--Microsoft had similar growing pains over a decade ago.

As anyone who's survived middle school can attest to, the in-between years are difficult but emboldening. Facebook stands the chance to learn a lot from its public image problems, disagreements with frenemies like Apple and impending battle over government regulation. And even though there are some haters, with nearly one-sixth of the world's population using the social network, Facebook is also the most popular kid in school.

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