Saturday, 1:05 p.m.
Todd meandered around the infield trying to figure out the best spot to post up for a significant amount of time. The way the infield was shaking out on that particular day, the third turn proved to be their best bet considering the crowd was a healthy mix of young professionals and college kids rather than locals and families.
Ben, overcoming his hangover beer by beer, notified the rest of the guys that he’d texted the girls from the night before against his better judgment. “What am I supposed to do?” he asked. “Just not try to hang out with these chicks?”
“Uh,” John stuttered, “Yeah, that strategy sounds about right.”
Todd checked his phone but to no avail. Whether it was the complete and utter lack of service or the lack of interest coming from Claire, Todd was conflicted on whether or not to be let down.
“I’m fucking starving,” Todd told the rest of the group. “Anyone else want anything?”
John nodded but was simply flying with Todd in an effort to get another julep. “Stay right the fuck here,” John explained to the guys as they departed towards the nearest stand. “Not trying to get lost.”
As they departed from the group, John walked alongside Todd and put another half of an Adderall in his hands. “I brought some of mine from work,” he told Todd. “I didn’t think Ben would actually give us any.”
“Great, just what I needed,” Todd said before slipping it into his mouth.
“Say,” John began, “We should hit up those chicks from last year – I bet your girl Claire’s here.”
“She’s not ‘my girl,'” Todd laughed off.
San Francisco, California
Friday, 10:31 p.m.
“Do we even know where we’re going right now?” she asked from the backseat of their Uber.
Alex looked over at Katie and smiled. “Yeah,” she clarified. “Katie, we’re going to that one bar you told us you used to go to during your internship, right?”
“Yeah, totally, Alex,” Katie responded. “I always went there during my internship. I couldn’t stay away.” She rolled her eyes.
She followed along on her phone trying to figure out where they were going. They were headed to a similar area as the night before – The Marina. “I swear,” she thought to herself, “If we go back to The Tipsy Pig…”
“Yeah,” Alex told the driver. “Right here’s fine.”
She looked through the window and up at the sign outside of a dingy looking bar.
“Ugh, I remember this place,” she muttered while the girls piled out of the car. “The fucking Horseshoe.”
They approached the door where a large man was checking IDs. Checking each ID of every guy going in meticulously, he finally looked the four girls up and down and waved them directly in. “You’re good,” he commented without looking them in the eye. What they saw upon entering was pretty much the opposite of what you’d expect in The Marina – a dirty bar where ordering anything but a draft or a shot would come off as uppity, a slew of pool tables in the back, and bathroom where you’d be crazy to do anything but squat.
“Why the fuck are we here?” she asked trying to jockey for position at the bar.
“There,” Alex pointed. “That has to be them.”
Saturday, 2:11 p.m.
He turned the brightness all the way up on his phone as the Kentucky sun beat down on them harder and harder.
“Hey!” he read. “We just got here – where are you guys watching from?”
John hit him on the shoulder and asked, “Why do you keep looking at your phone? There’s, like, zero fucking service in here. I’m on airplane mode if you need me.”
Todd shrugged and tried not to act like he was texting with anyone, but considering he had read receipts on and there was truly no service, he had to respond before his bars went back into oblivion.
Ben looked over Todd’s shoulder at his phone’s screen and asked, “Who the fuck is ‘Claire’?”
Each of the guy’s backs straightened out and their mouths were a combination of shock and smile. John took his sunglasses off his face and looked directly at Todd – “You fucking dog. Is she here? Tell me she’s here. Tell me she’s fucking here.”
San Francisco, California
Friday, 11:01 p.m.
After exchanging awkward hellos and pouring themselves Anchor Steams into plastic cups, she dragged Alex into the tiny bathroom.
“How the fuck did you do this?”
Alex smiled with a closed mouth and a sly look in her eyes. “Oops,” she said.
“I can’t tell if I hate you, or love you because you’re so fucking ridiculous,” she told her while fixing her hair. “Does Trip know you’re texting random bros in San Francisco or…?”
Alex laughed before assuring her, “I’m sure whatever I’m doing right now is nothing compared to what they’re doing at Derby. But, like, does Todd know you’re putting your number in random bro’s phones or…?”
“Okay, yeah, it’s decided – I hate you,” she snapped back attempting to hold back a laugh.
Saturday, 3:05 p.m.
“Todd!” Claire yelled from afar. There was no way he’d possibly recognize her in the massive crowd considering the size of her hat (and the size of her sunglasses). Separated by about twenty rows of people between them, she slid through the crowd followed by what appeared to be her group of friends.
John slapped Todd square on the back attempting to jar him, but instead feeling that Todd’s back was drenched in sweat. “I fucking knew you had a crush on this girl,” he whispered with Claire moving closer.
“Todd turned and shielded his mouth so no one could see or hear him except John. “I don’t have a crush on her,” he reiterated. “I just figured she’d be better than those trolls from the night before.”
“Yeah,” John laughed off. “Okay, bud.”
She got closer and closer while the other four guys made jokingly inappropriate comments behind him. “She looks good, Toddy Boy,” one said. “Look at that tan she’s rocking,” another said. It got to the point where she was so close that Todd had no other move but to hush them.
“Todd!” she yelled again, now face-to-face with him, going in for a hug. “How are you? I can’t believe we actually found each other in this crowd.”
“Right?” he responded awkwardly, praying the other guys behind him wouldn’t say anything stupid.
Trip, John, Ben, and Finn started shaking hands with the other people in her group after Finn jokingly said to Claire, “Claire, always a pleasure. From what they could tell, it didn’t appear as though she was with the same group as the year before – Lindsey and Rachel were absent – but the five or six people she appeared to be with looked fun, at least.
“Name’s Trip,” he said while shaking everyone’s hand. “Glad to meet you,” to one. “Good to see you,” to others.
Claire said her hellos to the guys she kind-of-sort-of remembered meeting the year before, as Todd introduced himself to the rest of her friends.
“Todd, was it?” one asked. “I’m Grant, Claire’s boyfriend.”
San Francisco, California
Friday, 11:16 p.m.
“You don’t remember my name, do you?” he asked her, this time not in his blazer and jeans but in a short-sleeve button down and a Giants hat.
“Uhhhhh,” she hesitated.
“It’s Jordan,” he interrupted, knowing exactly the situation from the night before. “I don’t blame you, you girls were pretty tuned up when we arrived.” He looked down at her oversized iPhone in her hand. “I thought your phone was dead which is why you texted me from your friend Alex’s phone?”
She looked over at Alex who was eavesdropping on the conversation. Alex brought her hand to her face and turned away laughing to herself (and to Katie).
“Uh, nope,” she awkwardly laughed off. “I think Alex did some investigative work.”
“I don’t even think I want to know,” Jordan told her. “You want to reintroduce ourselves over a shot of Fernet?”
Saturday, 3:10 p.m.
“Nice to meet you, man,” Todd told him.
Todd felt emotionally helpless. Not helpless in the sense of being sad, but in the sense of the Adderall taking emotions out of his system and the confusion of whether or not to be surprised, let down, or happy regarding Claire’s relationship status. While the two groups exchanged pleasantries at the tail end of a line to get more drinks, Todd ran the situation through his head. His feelings on the everything all boiled down to trying to figure out why he texted her in the first place.
Did he want to hook up with her, he wondered. Was he doing it out of resentment for his relationship being “on a break,” or was he trying to meet up with her to take care of what his friends considered to be “unfinished business” from the year before? He felt guilty. After all, he was going through a break, not a breakup.
She tapped him on the shoulder. “You’re awfully quiet – need another drink?”
“Ha,” he laughed off. “Yeah, I think another drink is exactly what I need.”
San Francisco, California
Friday, 11:22 p.m.
“So what’s your story? Was that whole ‘yoga retreat’ thing just a joke or…?” he asked after requesting their shots from the bartender.
Embarrassed by the fact that they skipped, she debated whether or not to tell the truth – that three bottles of rosé had spoiled three thousand dollars worth of a vacation.
“Ha, no,” she uncomfortably laughed off. “We, uh, skipped because we were a little hungover this morning.”
He smiled. “Well, I can’t say I’m all that upset about that.”
Saturday, 4:55 p.m.
Todd took a long, maybe too long, sip from his fourth (or fifth) julep of the day. He couldn’t remember, and he didn’t really care. By this point, it became clear that his group and Claire’s group were going to conquer the day together. He had already had numerous conversations with both Claire which consisted of generic “so how’ve you been?” empty conversation where John did fake hump motions in the background while her boyfriend wasn’t looking. He had also talked to her boyfriend, Grant, in that same vein. He learned exactly what you learn about someone when you just meet them in a party situation – where he went to college, what he does for a living, how long they’ve been seeing each other. You know, shit you don’t give a fuck about.
Standing alongside both of them, Todd asked Grant, “So who’ve you got your money on?”
“Eh,” Grant brushed off. “Not much of a betting guy myself.”
The conversation halted only to be broken up by Todd muttering, “Cool,” and dragging even more silence out.
“What time does this thing start again?” he asked Todd.
“We’ve still got the Turf Classic and one more race ahead of us,” he said looking forward toward one of the giant television screens surrounding the track. He lifted his julep glass in front of him before turning to Claire and Grant. “I’m going to go get another – either of you want anything?”
“Eh, we’re good,” she told him.
San Francisco, California
Friday, 11:45 p.m.
After taking their shots, they stood at the bar engaged in conversation while the rest of their group lingered between the bar area and the pool tables. Her nervous ticks were kicking in and she kept checking her phone between statements like, “Oh my God, that’s crazy,” and, “Wow, that’s so funny,” in order to keep the conversation flowing. Whatever chemistry existed the night before had started and ended at The Balboa Cafe.
“Can I tell you something?” she interjected, having no idea what sentence of his she even interrupted.
“Like, this is probably super awkward because I don’t really know anything about you, but I think you should know that I have a boyfriend.”
He laughed in the way that guys laugh when they realize that their efforts are fruitless. “Ha, I mean, that’s totally fine.”
“Sorry,” she apologized. “I know how weird that was. I just, like, needed you to know that this isn’t happening.”
He thought it was happening, but he also wasn’t the type to be an asshole about it.
“That’s fine,” he assured her. “That’s totally fine. Let’s go get back with the group, play some pool, and enjoy each other’s company, yeah?”
“Yeah, that sounds great.”
Saturday, 6:31 p.m.
They pushed more and more forward trying to get as close to the gate as possible in hopes of seeing at least a flash of the horses. “My Old Kentucky Home” had just blasted through the venue’s speakers, and Todd, John, and Ben lead the group which still consisted of the friends they’d met up with. Looking back, John tried to ensure Claire was out of earshot.
“So, uh, Grant, huh?” he asked.
Todd knew exactly what he meant.
“Yep, good guy,” Todd said.
“Honestly,” John began reluctantly, “It’s probably better that way.”
“Better what way?”
“Like, you didn’t need to hook up with her. That would’ve been kind of shitty on your part and I didn’t want to be the one to tell you that just before it happened.”
“Yeah, agreed,” Todd told him while putting his hands through his hair. “Blessing in disguise. Would you have really stopped me?”
John patted him on the back again, and again feeling the beads of sweat caused by the sun.
Yeah, buddy,” he confirmed. “Would you have actually gone through with it?”
Todd shook his head before verbally confirming, “Nah, I think I just wanted to know I could.”
“I think we both you know could’ve, man,” John said. “Now let’s just hope Gunnevera wins so we’ve got some money to blow on dinner and strippers tonight.”
The air at Churchill Downs turned to the air they’d felt the year before, and the air that everyone who’s ever attended the Derby had felt before them. An unmatched energy falls over the thousands of patrons as the horses load into the gate. The sun reached the perfect height in the sky where a Derby program serves as the perfect shade for your face. Todd looked down at his phone to see how long they had before they hit post time, realizing that it could all start at any moment. Just beneath the time, he saw he’d received an unexpected text before hearing a loud shot followed by the gates opening.
And they were off. .