I'm pretty sure this ad is seriously intended to encourage you to use LivingSocial.
I Googled LivingSocial and, believe it or not, it's actually some sort of Groupon competitor - not, as this ad might lead you to believe, a drug that delivers a powerful dose of estrogen to help kick-start your long-slumbering desire to transform into a woman.
This truly ranks among the most bizarre sales pitches I have ever seen. Sure, it's just intended to be funny, but you're not Budweiser, LivingSocial. You can't just do whatever you think is humorous; you still need to sell your product. Not enough people know who you are yet. And while there is a small segment of the population for whom this pitch might make perfect sense, the vast majority of people are not watching this and thinking, "Oh, sweet, LivingSocial's deals are so great they will help a bearded Deadliest Catch-type turn into a transvestite! I gotta get me some of that sweet deal action!" They are almost certainly thinking what I thought when I saw this, which is, "That is fucking weird."
And realistically, LivingSocial clearly does not disagree with that. All this ad is really doing is using the idea of a man becoming either a transvestite or a transgendered individual to get cheap laughs. This strikes me as just a little inappropriate. It's kind of interesting to chart the groups you can and can't get away with using as punchlines in commercials - you couldn't get away with making gay or racist jokes anymore; you can still get away with making fun of the genders because they're such broad groups. And apparently you can also get away with jokes about transvestite/transgendered people, presumably because they're a pretty small segment of the population and because most people still regard that behavior as particularly abnormal.
The idea of this guy transforming into a woman - eating and enjoying cupcakes! Doing yoga! Getting waxed! - is clearly supposed to be side-splittingly hilarious. But I don't think so. To me it feels cheap - like the live-action equivalent of Dodge's "Man Bag" commercial narration, which actually mentions a yoga class as something unmanly - and borderline offensive to the population it's ostensibly depicting. Especially because, I mean, we're talking about something that I assume is a momentous decision for the individuals affected... and here's LivingSocial suggesting that all it takes to open up to your true self is a few good coupon deals. Ick.
Whatever. The irony is that with this ad being so bafflingly strange, all Groupon really had to do was make a passable ad with their Super Bowl entry and they would have easily won the category for the night. Of course, we all know what Groupon actually did - so maybe LivingSocial comes out ahead anyway.