Have you seen Microsoft’s new commercial? Dubbed “Child of the 90s,” it is especially worth the minute and a half of viewing time if you, like me, were in fact a child of the 90s. The opening text flashes on the screen: “You might not remember us. But we met in the ’90s.” Then follows a video montage of the most memorable cultural artifacts that defined the Millennial childhood: pogs, peace signs, Lisa Frank, floppy disks, Tamagotchi pets, Lunchables, and of course, the computer game Oregon Trail (recalling painful memories, no doubt, of dysentery and cholera for many a 90s middle school student).

A nostalgic stroll down memory lane for those born after 1983? Yes. An effective piece of marketing for Microsoft’s Internet Explorer? Eh, not so sure. The commercial ends with a visual of Microsoft’s still relatively new Surface tablet, followed by more text: “Reconnect with the new Internet Explorer.” Clearly this commercial is targeting Millennials; inviting us to revisit a brand we discarded – along with our windbreakers and fanny packs – in favor of Microsoft’s number one competitor: Apple.

The ad reminds me of people who have long since graduated but still hang out at their old college bar, relying on the nostalgia of glory days and standing out like a sore thumb despite their best efforts to assimilate to the tastes and trends of the younger generation (David Wooderson from Dazed and Confused, anyone?). We all know these people. Their behavior is completely obvious to everyone. Except them.

The problem Microsoft has can be best illustrated by a comment I read on my own Facebook newsfeed, in response to this commercial: “This is great! Still using Google Chrome though. Sorry!”

While fun and nostalgic, Millennials are not rushing out to buy pogs or walkmans, so why would they consider using an Internet browser associating itself with those relics of the past? Especially when Internet Explorer 10 obviously doesn’t run on Apple devices. Microsoft is asking Millennials do a lot more than try a new browser. The company is asking them to consider an alternative to their iProduct-dominated lives, and that is a tall order.

So what could Microsoft have done differently? Perhaps instead of trying to win over an entirely new demographic of consumers right out of the gate, they could have employed the same marketing strategy (appealing to the consumer emotionally) and targeted consumers who would be more responsive to actually trying the new Internet Explorer, first. Or, if they still wanted to target Millennials, Microsoft could have taken a less direct approach. Instead of trying so hard to relate to Millennials by saying “We remember Oregon Trail, too!,” Microsoft might have instead considered some content co-creation strategies and campaigns that would have allowed consumers to help dictate what the Microsoft brand means to them.

There’s no doubt Microsoft is stepping up its game in turning out products that can compete with Apple (the Surface is actually pretty cool), but this commercial makes it clear just how important messaging and brand positioning are to the success of introducing any new product into a new market.

What did you think of Microsoft’s “Child of the 90s” ad? Does it make you want to try the new Internet Explorer, or did it just remind you how much you loved snap bracelets?