First came the awkward placement of the HP TouchPad into the season premiere of The CW’s Gossip Girl.  Leaving aside the oddity of these characters using the TouchPad rather than the iPad, the promotion garnered attention because HP decided to get out of the PC business (including killing the very technology used by Serena) several weeks before the GG premiere.

As Advertising Age reports, this is the problem of the production schedule–placement deals are worked out months in advance, and sometimes by the time they air they’re already out of date.  The Ad Age piece cites Modern Family‘s spring 2010 integration of Toyota, a promotional effort that came to fruition at precisely the same time as Toyota’s massive recall PR nightmare.  In the case of both HP and Toyota, these promotions were developed into the storyline and filmed up to nine months in advance of their airing, making any changes in the final months an impossibility.

On the heels of the Gossip Girl awkwardness came the two most recent episodes of NBC’s The Sing-Off.  For the past two weeks, contestants competed with their interpretations of a current chart-topper and a 1960s hit.  The latter was being used as a cross-promotional opportunity for the network’s The Playboy Club, which aired in the 10 p.m. Eastern slot directly following the a cappella competition.  The end of the first episode featured host Nick Lachey exhorting, “If you enjoyed our ’60s songs, be sure to stick around for more of the decade and watch The Playboy Club, coming up next!”

When news of The Playboy Club’s demise came the following day, the promotion seemed like an awkward but charming moment, but this week’s episode of The Sing-Off–filmed over a week prior, mind you–was almost uncomfortable.  As the ’60s performances commenced, Lachey addressed his costume change by noting that the slick suit he was wearing had come from The Playboy Club‘s costume department.  As I fought the giggles (thinking that the costume department was probably happy to get rid of it as they cleaned house), it got even more awkward–at the moment Lachey finished this comment, a graphic appeared on the bottom of the screen, informing viewers that up next was Prime Suspect.

These two virtually concurrent instances of awkwardly out-of-date product integrations reveal two key truths about the nature of television advertising.  First, that the television production schedule requires a great deal of pre-planning on the part of advertisers, studio executives, and writers.  Second, that as product placement and cross-promotion become the norm due to ad-skipping with DVRs, DVDs, and online streaming, we’re not only going to see more integrations, but more moments when those placements just don’t work by the time they hit the air.

In the meantime, let’s get Serena and Blair some iPads, and hope next week’s episode of The Sing-Off doesn’t feature a cappella versions of songs about workplace romance.