Triple Crown: 3 Tips for Getting Lucky at the Races

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As “I’ll Have Another” streaked home for the Kentucky Derby victory earlier this month, I could not help but notice the Cro-Magnons on the infield.

Growing up in Baltimore, I’ve attended many infield parties at the second leg of the Triple Crown, the Preakness. Something about that infield makes us all behave like heathens. Don’t get me wrong — it’s a good time (even though it feels a bit like a war zone). Hook-ups abound, and there are plenty of opportunities to merge with the opposite sex. If you want to get lucky:

Rule 1: Keep Your Clothes On

Sounds contradictory, right? Most guys there would tell you they don’t want you to keep your clothes on; most guys who attend infield parties in fact arm themselves with a few supplies: a well-stocked cooler, sunglasses, sunscreen, and a sign reading “Show Your Tits” (usually classily scrawled in sharpie on a piece of cardboard). We’ll call them boob-hunters.

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A good boob-hunter will look for the mob and turning heads chanting “show your your tits!” with the help of their signs, of course. Even when you’re mid-conversation with a friend, they may cut you off and look over your shoulder as if they see a ghost: “Over there!” Usually, the main indicator is that a woman has been hoisted upon some guy’s shoulders. But even guys (like myself) who get a kick out of the Preakness flashers would never actually date the type of girl who was willing to show herself off (drunk or not) to a crowd of salivating savage men.

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Rule 2: Dress Accordingly

One of my favorite things to do is dress over-the-top preppie as if I’ve got cash. Horse Racing is the perfect opportunity. I admit, looking for ridiculoud preppie outfits is as fun as boob-hunting. If you’re not going to go ultra-prep, just dress like you’re going to a sunny sporting event.

One year, we invited a girl named Melissa, who I had a crush on, to attend Preakness. But Melissa showed up wearing a white sweater, pearls, and heels for an infield party…on the grass. Don’t get me wrong — she looked great. But it wasn’t the right look for Preakness. It told me a few things about her: she either tried too hard, or she didn’t do any research about what she should wear to the track.

Women who dress elegantly are attractive, but sometimes you have to go casual. Show you can do both looks, especially at outdoor sporting events. Do a little research if you’re not sure what to wear, because it’s awkward when you don’t do it right.

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Rule 3: Ask Yourself: “Do I Really Want To Conceive A Child At The Triple Crown?”

The Preakness infield is a primordial soup concocted of mud, sweat, beer, liquor, and other bodily fluids that I can’t bring myself to write. Most people bring chairs and picnic blankets to try to defend themselves against this toxic mixture.

It was in this bacteria-filled ecosystem that my buddy from college (Bird) and friend from high school (Lauren) met. After hanging out all day, the two ended up on a little makeshift picnic blanket (beer box) amidst a mud/beer/bodily fluid patch of dirt/grass on the Preakness infield, oblivious to the debauchery that swirled around them.

Little did we know at the time that the two would end up getting married. They have two beautiful children, but I can’t help but chuckle when I remember that they are — in some way — the product of the Preakness infield. If you want to avoid this, be safe. Or at least, in good humor, nickname your child after the winning horse.