It’s my first date in five years, and I’ve got to impress. That means I’ll actually have to brush my hair this time, and make the wings subtler. That means I can’t wear any of my sick T-shirts; the “There are 10 people in this world: those who understand binary and those who don’t” shirt, nor the tuxedo with a rose in a pocket square shirt, nor even the sick Average Joe’s T-shirt from the Dodgeball DVD are acceptable for this date. Polo shirt, or bust.
Furthermore, I am restricting myself from hats, wristbands, sweatbands, and bandannas for this one. I’m not trying to pick up some chick at a music festival this time: it’s a lunch date. And I’m paying. So I best not be paying with bad fashion. That means I can’t be wearing those white Puma socks you can get at bulk at Costco. Nope, fancy black socks are a must. And, to go along with that, some nice shoes. My beat up New Balances will tip the balance out of favor, I must wear my slick black Vans, no matter how uncomfortable. For she might be uncomfortable with the lack of style otherwise.
Finally, the most important clothing: what goes around the waist? Soccer shorts don’t have pockets nor style when it comes to higher-class dating. I will not be able to carry my wallet nor a conversation with those. Long pants will look like I’m trying too hard, this is simply a first date: we must be casual. That means there’s only one choice: I must wear only the finest of cargo shorts for this date.