A Wall Street Genius's Final Investment Playbook-Chapter 294: Side Story, Jessie (3)

‘Without a doubt… Rachel has feelings for Sean!’

Jessie was certain. Though Rachel had never said anything like that directly—no, there was no need to. Every time those two were together, the air between them always shifted into something strangely pink. And yet Rachel was trying so hard to hide her feelings. The reason was obvious.

‘She’s afraid that if things go wrong, even their current relationship might break.’

It was the kind of worry you’d find in a dating guidebook. Whenever feelings sprout between friends or colleagues, everyone inevitably starts thinking the same thing. What if things go south and it just gets awkward? What if I end up losing a friend for nothing?

But. Jessie already had a simple, clear answer.

‘If you’re already worrying about that, then you’re not “just friends” anymore.’

In the end, this kind of relationship was bound to cross the line someday. The real question was when. Jessie decided to give that timing a little nudge forward.

“Rachel, how about a movie night tonight?”

“Right now? You must still be tired…”

“Tired? From what? It wasn’t even a business trip, just a getaway. Besides, I suddenly feel like binging all my favorite movies tonight… what do you think?”

“Yes, I’d love to!”

When Rachel readily agreed, Jessie’s eyes lit up. The playlist was already perfectly prepared. Of course, the genre was romantic comedy! And every single story was the same. All of them were part of the “friends to lovers” series. After lining up three of those movies in a row, Jessie casually glanced at David at just the right moment and spoke.

“Remember? That was exactly us at the beginning, right?”

“You two?”

“Yes. I used to be super close with five of my dorm friends, and David was one of them. I worried a lot. If we started something and it turned awkward, it could ruin the whole group vibe. I might even lose a good friend.”

“Ah…”

Rachel’s eyes wavered. She empathized, but her expression also seemed to say, ‘So what happened then?’ Jessie smiled to herself with satisfaction. Of course she’d be curious.

“So back then, I tried a little ‘friend test.’”

“A friend test?”

“You know, those silly quizzes you see in magazines. The ones to check if someone’s just a friend or maybe more. I’m sure you could still look them up right now and find tons of them.”

Jessie pulled out her smartphone and started searching. As expected, the internet was full of them. She clicked on the most clickbait-looking post.

<No More Pretending to Be “Just Friends”! The Ultimate Relationship Reveal Quiz!>

“How about trying this one? You and Sean!”

“Eh, but we’re not that kind of relationship…”

“Then that’s what the results will show! Don’t worry, it’s just for fun, right?”

With a confident grin, Jessie tapped the link. Inwardly, she was already predicting the result.

‘At the very least, it’ll say “something’s going on”… or if we’re lucky, maybe even “definitely a couple.”’

But. The moment she read the first question, Jessie’s smile vanished.

Q. Skinship Level Check! How often does that person touch you?

A. Touch? What’s that? I’m not a touchscreen.

B. Sometimes a pat on the shoulder—solid coworker level.

C. Personal space? Never heard of it. We’re basically one already.

Jessie froze. She didn’t even need to think about it. The answer was A. Overwhelmingly A.

“Jessie?”

Rachel gave her a puzzled look as she stared blankly at the screen. Jessie quickly pretended to be calm.

“Oh, hold on. The internet’s slow… it’s still loading.”

Muttering something about the Wi-Fi acting up again, she scrolled further down. Maybe there would be a better question.

Q. At midnight, you text: “I can’t sleep…” What does he do?

A. Replies at 7 a.m.: “Hope you slept well” (read after 7 hours).

B. Reads right away: “Too much coffee again?”

C. Calls within 3 seconds: “What’s wrong? Want me to come over?”

This time she dropped her head. The problem was far worse than before. Send Sean a text at midnight? And something that personal, like “I can’t sleep”? Might as well text the White House. Of course, Sean had never officially announced a “no personal texts” policy… But it was an unspoken rule everyone knew.

‘Why are all these questions like this?!’

Grinding her teeth, Jessie kept scrolling. But.

Q. How does he react when someone else shows interest in you?

Q. What pose does he make when taking selfies with you?

Q. What does he do on your birthday?

The further she scrolled, the stiffer her face became. Every question only confirmed the distance and walls between the two of them. But at this point, she couldn’t very well say, “Oh, this one’s lame, let’s do something else”. Rachel was right there, bright-eyed, waiting for the “loading” to finish. Then Jessie’s eyes landed on the final question.

Q. The last time you were alone together, what was the vibe?

A. Strictly business. Share an Excel file, say “Good work,” and leave.

B. Something was different. Eye contact made you look away.

C. If it were a movie, 100% a kiss scene. Heart pounding like a drum solo.

Jessie suddenly brightened, reading it out loud with playful drama.

“Oh, there we go—it finally loaded. Question time! The last time you two were alone, what was the vibe?”

But then… why? As soon as she read the question and the choices… Rachel froze, then lowered her head slightly. And Jessie noticed. The tips of her ears had turned as red as a tomato.

“… …”

Rachel hesitated, unable to speak. Jessie smiled with deep satisfaction. That alone was enough of an answer.

“Oh, don’t worry if it’s awkward to answer. It’s just for fun anyway.”

Jessie smoothly put her phone away. She locked the rest of the “disaster quiz” before Rachel could see any more, then fumed inside.

‘What kind of love detector is this? Total scam!’

Anyone could see the pink fireworks exploding between Rachel and Sean! Aside from the last question, the rest were garbage. But still… Even this ridiculous test had its uses. Because through it, Jessie had stumbled onto an unexpected insight. She had finally pinpointed the real obstacle blocking their relationship.

‘The problem is Sean.’

***

Even for ordinary people, moving from friends to lovers always came with a sense of pressure. Crossing that line is never as easy as it sounds. But in Sean’s case… the level was completely different.

‘This isn’t just a line, it’s a wall… no, not even a wall. It’s basically the Himalayas.’

The aura Sean gave off could only be described as a massive snow-covered mountain plastered with a giant sign: “Restricted Area – No Unauthorized Entry!”

To make matters worse, Rachel wasn’t exactly well-suited to deal with that kind of barrier either. She was maxed out in consideration points, and she wasn’t the type reckless enough to climb such a sheer cliff barehanded.

‘That mountain… she’ll never be able to climb it alone.’

Which meant there was only one answer.

‘I’ll just have to be the sherpa!’

Even Everest starts with base camp. For now, the most urgent task was this: ‘Make it so she can text him casually, outside of work!’

She needed to get to the point where she could shoot Sean a quick message with no particular reason. That was priority number one. But while it sounded simple enough… In reality, it was an ultra-difficult mission. Jessie knew this painfully well from personal experience. Every time she’d text Sean for her “make him feel like family” project, she’d type, delete, re-type, and delete again over and over.

‘There’s no way Rachel would ever take the first step.’

She was too considerate, and she wanted to preserve her current relationship with him. But if those two were left alone like this, nothing would change until the next ice age. So a gentle push was needed. Luckily, the method was surprisingly simple.

“Rachel, didn’t you say Sean’s cooking was delicious? I’m dying to know—could you make it for me sometime?”

“What? But I can’t cook at all…”

“You said he just followed a recipe, right? Then just follow the recipe again. I’ll help you!”

“Ah, um…”

A flicker of discomfort crossed Rachel’s face. Jessie cheered inwardly.

‘Knew it! Sean has the recipe!’

Which meant Rachel would have to contact him to make the dish. Not for work. Not for Castleman business. But just for a recipe! Normally, Rachel would never even attempt such a thing.

…

“Please? I’m really, really curious.”

Rachel, kind as she was, couldn’t resist a heartfelt request.

“…Okay, I’ll ask him.”

As expected, Rachel carefully pulled out her phone and sent a message. And then—

Ding!

The reply came back almost instantly, as if he’d been waiting.

Here it is. (link)

Blunt, minimal, containing only the necessary information. But Jessie wasn’t focused on the dry content. What mattered was the speed. A reply in just ten seconds…

‘Faster than I thought.’

That meant he hadn’t hesitated at all before responding. It was a clear, positive signal.

‘He never answered that fast when it was me.’

It was annoyingly unfair, but that didn’t matter right now. Jessie could barely contain her excitement.

‘This is it!’

As the saying goes: make hay while the sun shines!

“Could you ask him if he followed the recipe exactly? Like—was the milk whole, 2%, or nonfat? And the butter—salted or unsalted…?”

“What? Th-that specific?”

Rachel looked flustered at such nitpicky demands. But in the end, she couldn’t resist Jessie’s pleading eyes and fired off another round of questions to Sean.

“Are we bothering him too much…?”

Rachel looked uneasy, but Jessie was cheering inside.

‘Perfect! What matters is taking the first step!’

The first time is always the hardest. The second time would be much easier. Now that a precedent had been set, casual texts would become far less daunting in the future. Of course, this alone wasn’t enough to conquer Everest. At best, they’d just stepped out of base camp. The next goal was the mid-camp.

‘They need regular excuses to meet! Not for Castleman, but purely personal reasons…’

Naturally, Rachel would never pester Sean for personal matters. But what if… it was for Jessie’s sake?

“Rachel, I actually have a serious problem. Can I talk to you about it?”

That’s how the counseling session began.

“The truth is, I really want to be like family with Sean. But it feels like he’s avoiding me… He even refused my Christmas invitation. Am I being too much for him?”

If Jessie asked Rachel to act as a go-between for improving her relationship with Sean… Then whenever something came up, Rachel would step in. Which meant more opportunities for private meetups. In reality, it was little more than “counseling designed to set up meetings.” But Rachel ended up giving some unexpectedly sharp advice.

“Hmm… maybe it’s a cultural difference. For Americans, days like Independence Day or Christmas are important. Sean moved to the States in middle school, right? Maybe you should celebrate Korean holidays instead.”

And then—Rachel dropped the real bomb.

“For example, Chuseok—it’s kind of like Korean Thanksgiving. Sean once told me that it always reminded him of meals with his parents. What was the name of the dish again…? Ah, bibimbap! And Korean-style pancakes…”

Jessie’s eyes went wide.

“Wait! You mean Sean actually… talked to you about foods tied to family memories?”

“Uh… yeah. We even went together once, since he didn’t want to eat alone.”

“When was this?!”

“His first Thanksgiving after joining Goldman.”

Unbelievable. Jessie was floored. Sean, who always threw up steel walls at the mere mention of family… Had opened up and shared those personal memories freely—with Rachel. There was no doubt anymore. To Sean, Rachel was someone special. But that wasn’t even the end of it.

“I think Sean’s more used to giving help than receiving it.” 𝐟𝕣𝗲𝕖𝕨𝗲𝐛𝗻𝗼𝐯𝗲𝚕.𝗰𝚘𝐦

“…Sean?”

“Yes! If you really want to get close to him… why not go to Sean directly for advice? For example, aren’t you worried about graduate school these days?”

“Well, I don’t think he’d like that very much… Besides, even if Sean is talented in many areas, counseling isn’t exactly…”

But Rachel firmly shook her head.

“No. Sean only sounds cold when he speaks, but in reality, he’s actually really good at this kind of counseling.”

“…Sean is… good at counseling?”

“Yes. In fact, the reason I even dreamed of working at a gallery was all thanks to him.”

“What?!”

Jessie had never heard this before.

“Yes. Art was my childhood dream, but I gave it up because I lacked the talent. When Sean heard about that, he told me to look for something connected to my dream that I could still do now… and that’s when he recommended gallery work to me.”

And the revelations didn’t stop there.

“On top of that, Sean even helped me with my brother.”

“Your brother… Gerard?”

“Yes. Gerard was in a bit of trouble because of some family issues.”

Rachel cautiously shared a story about the Marquis family. She left out the finer details, but it was enough for Jessie to understand the general context. And what she heard left Jessie stunned.

“Wait, so you’re saying… that ‘currency war’ Sean waged in China… was actually done in the process of helping your brother Gerard?”

Jessie was speechless. That incident had shaken the entire world. A showdown against none other than the colossal nation of China… and it had all been sparked simply to help Rachel’s family?!

‘Sean… just how serious were you!’

Jessie quietly reflected. She had been meddling, thinking the two of them were frustratingly stagnant, when in fact there had never been any need. It made her feel embarrassed. As it turned out, Sean and Rachel had already been building extraordinary trust and affection with each other for a long time.

How could she have possibly known? But it was all true.

Sean, who never shared family matters with anyone, spoke openly about them with Rachel. He listened to her life worries seriously and gave her courage. He even risked taking on enormous dangers for her family’s sake. And Rachel understood Sean’s sincerity better than anyone else, always grateful and deeply reliant on him.

Wasn’t that already enough? Two people who had built such a deep bond didn’t need to be forced closer. They would naturally grow closer on their own. That meant Jessie’s job was simple.

‘All I need to do is create more excuses for them to meet.’

“Then… how about spending the next Korean holiday in a Korean way? I looked it up, and it said people eat rice cake soup on New Year’s Day. Let’s make it together!”

“Sure!”

But when Rachel glanced at the calendar, her expression suddenly darkened.

“Uh… I don’t think I can. I have a family gathering that day.”

“Can’t you just say it’s important and skip it? Wouldn’t they understand if it’s for Sean?”

“No, the thing is…”

Rachel confessed carefully, looking troubled.

“It might actually backfire. My family… they don’t really like me seeing Sean.”

“What? Why not?”

Considering that Sean had gone so far as to risk everything to help Gerard, there shouldn’t have been any reason for her family to dislike him. Where in the world would you find a son-in-law candidate like that?! But soon Jessie had to nod.

‘Ah, right. That does make sense.’

Rachel’s family had always been a bit extreme. Especially her father and her brother…

When Rachel first began staying at Jessie’s house while commuting to Philadelphia for the Castleman illness issue, her family had once shown up saying they “needed to see for themselves,” and essentially gave her a kind of “interview.” Even then, the way they looked at David had been far from ordinary.

But it wasn’t because they didn’t trust him. It was purely excessive overprotection toward Rachel.

‘If they were like that even in front of David, a married man… imagine how they’d be in front of single Sean.’

In that moment, Jessie realized something. The greatest obstacle between Sean and Rachel… might not be Sean. It might not be Rachel either. It could very well be the Marquis family itself.

But then again—

‘That’s just how family is.’

Annoying, inconvenient, complicated, and meddlesome beyond reason. The Marquis family would undoubtedly keep trying every trick they could to interfere with Rachel’s love life. And yet strangely… Jessie found herself smiling.

‘An eye for an eye, a tooth for a tooth! Meddling against meddling!’

If family was going to get in the way, then she’d just fight them as family. Luckily, Sean now had a new family to back him up—David and Jessie themselves.

‘All right then, bring it on!’

Jessie’s determination blazed. She wasn’t worried. If it came down to a meddling battle, there was no way she would ever lose!