It ain't what you do, it's the way that you do it.
~The Fun Boy Three feat. Bananarama
Self-awareness is a tricky thing. Too much and you hold yourself back from doing great things. Too little and you do things that make you look like a schmuck. Case in point: The Rosedale Club.
Getting dressed up and going out to share strong drinks and stronger opinions sounds like a great evening to me. Throwing cigars and (explicitly) scotch in the mix, because they're so frequently associated with old white guys talking about how fucking great it is to own land, biases how people will see the entire evening towards that stereotype of old white men. It's awesome but irrelevant that the organizers are taking steps to make it inclusive, and I don't doubt their intentions, even if some of their defence sounded like a Colbert outtake. Framing anything you're trying to do in the context of something you're not... is no different than rappers wishing they were Tony Montana or me wishing I was Ryan Gosling in Crazy Stupid Love.
Which I totally do. But I admit to it. I don't give myself the excuse of saying it was ironic if it all blows up in my face. It's not a joke. I think Ryan Gosling's a very handsome man, and thinking of how I compare to him gives me motivation to eat better and work out. I give my barber a photo of him when I go in for a trim, and no, I'm not making a word of this up. It's this picture, and this one when he asks for a second angle.
This shouldn't bug me, because it's happening in Toronto, but as a (relatively if not formally) young Liberal, it does. Whatever your opinion of Zach Paikin, he is one of the loudest young voices in the party. He gets published on iPolitics and does news appearances. He has a Fan Page. So, Zach, please: as someone who wishes you nothing but the best, because however you're perceived, I'm perceived by association? Stop trying to make the things you do look cool. It comes across as trying too hard and gives people an opportunity to dismiss what you're doing when it's actually a pretty cool idea.