By the time you’re reading this, the Kentucky Oaks and Derby will have come and gone and the festivities will be memories, but the hangovers and the pain from the empty caverns of our wallets will linger. I know, I know, you’ve delved into many a recap in the past 10 days since the first weekend in May, but you haven’t read mine, so sit down and shut up. Only kidding, my dears, but in all honestly, I was thrilled to trade in my bar stick for a racing program on Oaks Day, as LEO was kind enough to get this little barkeep a press pass for me to enter the depths of the Twin Spires and the sea of pink for the day.
On that first Friday, it was frigid and raining. Alas, my partner and I, along with our friends, Meg and Bridget, donned our most dapper duds, threw ponchos over our fascinators and set out for what could only be a day of quintessential Kentucky greatness.
Jamie and I began at Meg and Bridget’s house for some delectable Red Hot Roasters light roast with Ballotin Bourbon Ball Chocolate Whiskey, and, while I’m not one for flavored whiskeys, I’ll allow an exception in coffee and on Derby weekend, as this velvety, rich delight seemed to be the perfect way to start our day. Then, a quick mimosa (and maybe a shot of Woodford? I’ll let you decide), and we’re out the door to a friend’s property, just blocks away from the Downs. We begin the trek from somewhere near Longfield to Gate 3, and it’s more than just sprinkling. Trudging through puddles, I’m glad I wore waterproof Timberlands, and I’m glad I took that bourbon shot to keep me somewhat warm (yeah, I did). Some of our comrades are in open-toed shoes and shorts. It’s colder than a witch’s tit. I grasp my breasts: “There’s a 30 percent chance that it’s already raining.” I do have ESPN, after all.
We made it through Gate 3 unscathed, and Bridget turned around to ask, “Drinks or bets first?!” “Drinks!” I exclaimed, a bit too enthusiastically, and we found our way to the nearest $14 mint julep station. Because one must have at least one mint julep whilst at the Downs on Derby weekend, am I right? The four of us huddled together to begin to examine our bets, and Jamie and Meg are quite serious about their joint trifecta box choices until they realize they’ve analyzed the horses for race No. 1, when in actuality, it’s 1 p.m., and we’re on race No. 6.
Yup, it’s tampon time.
No, this isn’t an article about my menstrual cycle on Oaks Day, don’t fret — “tampon time” means it’s the perfect moment to whip out the fake tampons that double as booze tubes full of bourbon that my friend, Michelle, graciously let me borrow, and I was able to get through security (sorry, Churchill Downs). In all actuality, I was really hoping security would pull them out and begin to question me about the abnormally large tampons at the bottom of my purse, so that I could create an uncomfortable, public scene about my uncontrollably heavy flow. That would have been gold. Alas, bourbon shots in the Paddock with my friends — much better.
Sufficiently buzzed and unfazed by the weather at this point, I decided to peel off and take advantage of the various places my press pass would allow me to go, just because I could. I meandered onto the media parlay, the rooftops, the third floor and eventually ran into a friendly bar-regular friend of mine. He invited me up to the Jockey Suites, and, somehow, I ended up among an apparently-famous boy band and various other so-called celebrities. I found myself in the very suite of the financial institution that I bank with, which seemed hilarious to me. If only they knew my account balance. I ate a free crab cake and had a few bourbons on them (that’ll teach you, overdraft fees!), and something about it felt icky. I’m up here, warm and dry with a bunch of boring-ass white people, congratulating one another on being rich. I got a few fake introductions and compliments on my outfit from people who truly don’t give a fuck who I am, and I decided to find my out: Where are my people? I made my Irish exit and scurried down flights of stairs and escalators to find my crew, who’d just returned from the Infield, drunk and muddy, making bets and laughing and embracing. I felt like I’d been gone for an eternity. Because, sure, the Kentucky Oaks is about the ticket and the hat and all the trimmings, but more importantly, for me, it’s about the company you keep.