The walk back to the valet was quiet, Lana and Jack both deep in thought. Lana glanced at her phone and saw a response from Chloe:

Chloe: LOL don't be so dramatic, but fine, confirming I will call the cops if you're not home by 11! Have fun girl! I'll be home soon, so come over after! We need to debrief.

Lana finally broke the silence after Jack handed his valet slip to the attendant."So, what does the winner of this fantasy football league get?"

Jack's mouth raised in a half-smile. "A hundred thousand dollars."

"One hundred thousand dollars?" Lana repeated incredulously before her jaw dropped. "Are you serious?"

Jack laughed. "Yeah, I know. It's high stakes."

"Have you ever won?"

"Nope. But I keep losing money each year because of it. So, that's kind of annoying."

"I thought you were so amazingly good at managing your money?" Lana said sarcastically.

"I am," Jack said curtly. He looked away quickly, seemingly offended. "Again, I'm not perfect, and I still do idiotic stuff occasionally. I'm not proud of it." Lana stayed quiet as the valet pulled up in front of them with Jack's sleek black BMW.

The ride to Jack's apartment was mostly silent. Lana subtly glanced sideways at him and thought of how differently she expected this night to pan out. She began to take in his presence near her, like how his suit clung to his body and the strength he seemed to carry as he drove through the surrounding streets.

She could see his brows furrow as if he was lost in thought and debated if she was too harsh with him earlier. Maybe not... Ugh, I don't know!

No matter how much she wrestled in her head with how she felt... a small part of her still empathized with Jack. She wondered if her empathy was only because he was so handsome. As if somehow his looks gave him credibility as a person... which she quickly brushed off as a terrible justification for his actions.

But why does he have to be so handsome? This would be way easier to forget about if he didn't look like that...

Lana continued to trail down a rabbit hole in her head when Jack turned and noticed her staring at him.

"You good?" he asked cautiously.

But Lana hadn't even realized she was staring at him. Her train of thought had led her to wonder how big Jack's muscles are, and she quickly snapped back to reality after she heard his voice. "Oh uh... yeah. I was just wondering...  what did previous years' losers have to do? Is it something illegal each year?"

Jack's half-smile returned. "Hmm, let's see. I think, yeah, it's typically borderline illegal. Last year, the loser had to go streaking down Hollywood Boulevard midday. That was a tough loss for Emmett, but he took it well. He and his derriere made the news that night."

Lana smiled, imagining people's reaction to an adult man running down Hollywood Boulevard naked. The ridiculousness of it all was comical at that point. As they waited for one of the stoplights to turn green, Jack turned to face Lana. Something in his eyes drew her in, and his gaze penetrated through to her core.

"Lana, I know you said we wouldn't work out. And I completely understand your reasoning, but I hope that doesn't put the possibility of being friends out of the picture?"

Friends? That's awfully bold to ask. "I don't know, Jack. This all seems just a little too much for me to handle. I don't know how I can trust you."

"Okay, fair enough. But I'd at least like to try and make it up to you. Is there anything that I can do to show you that I'm a trustworthy person?"

"Get me my box back," Lana quickly replied.

"Well, of course. Anything else besides that?"

Lana paused and was surprised that something did come to mind. "Actually, there may be one thing."

"What is it? I'm one hundred percent in whatever it is!"

"Since your job is helping people manage their money, I was wondering if you could give me some financial advice?"

She recognized how bizarre the request was under the circumstances... but her financial situation was not great... so why pass up the opportunity for help from a professional?

And it is strictly professional. It's just business. Nothing to do with his looks... probably... I still hate him...

Jack looked back at Lana and seemed so beyond pleased with her question. "Absolutely, can do! We can even start now!"

Lana cracked a smile. It was kind of sweet how Jack's reaction made it seem like this was something that would be very fun for him.

"Tell me, why do you feel like you need help managing your money?" Jack said, eager to get started.

"Oh, you're serious? Like right now? Oh, uh... well... I guess I just want to be at a point in life where I don't have to think about money. I can just live normally without having to worry about questions like... Am I spending too much? Or am I saving up enough? Should I be buying Mega Millions or Powerball lottery tickets? And what's an NFT? Is that a crypto? How do I find a Bitcoin?"

Jack chuckled and massaged his head as if he just realized he had his work cut out for him. "I think there's a lot to discuss here. Let's start with what your specific financial goals are."

"I don't know... I guess... you know, I sort of have this dream." Lana tried to avoid eye contact, and her face grew hot.

"And...? Are you going to tell me what the dream is?" Jack asked playfully when he realized Lana was finished talking.

"Oh... well... I love the beach and would love to buy a house on the beach someday. I also love to bake and think it would be so fun to open a cute little bakery by the beach. I know people don't typically think of croissants when they're surfing, but places like Santa Monica have tons of little cute sidewalk cafes like that." Lana glanced over at Jack and saw him smiling. She immediately regretted sharing something so personal. She hadn't even told Chloe—her best friend—about this dream. And here she is, sharing so openly with a criminal. "Forget it. It's dumb. I know."

Jack's expression was hard to read. "No, no, it's not. Not at all. That's an awesome dream to have!" Jack smiled supportively.

This friendship thing may not be so bad after all. "So, what's your big financial advice for me?" Lana asked.

"Mmm, on second thought, I don't know if I can help you. I think your case is beyond repair," Jack said as he continued to smile.

Lana playfully hit his shoulder. "Okay, no seriously, Jack! I need help!"

"Okay, okay, yes I can easily help you and give you some financial advice. The only thing is it's more of a long sit-down conversation, and we'd need to go into detail about your income and expenses."

Lana couldn't tell if Jack was just trying to secure more time with her in the near future. Wouldn't be terrible, would it?

Lana responded like a pouty 5-year-old, "Ugh, can't you just give me the secret now?"

Jack laughed. "If there was some magical secret, I think I'd be out of a job."

"Okay, fine. I appreciate you helping me. I'm excited to learn more about it. I never felt like I was truly prepared for the adult world and managing finances. They don't teach you those things in school."

"I think it's one of those things that people sort of learn from each other." Jack paused for a moment and then continued, "Aren't we all glad that we ended up on this date tonight so that you can force me to give you free financial advice?" Jack said before dishing out a smirk. Lana knew he still felt guilty about it all, most definitely trying to find the silver lining to make it seem less bad.

The rest of the drive to Jack's apartment was far less tense. They chatted about finances for the remainder of the trip, as if there was never any drama earlier in the night.

The car pulled up to a tall, towering building near Beverly Hills which overlooked the surrounding area. The glass paneling reflected the shining lights from the city and the night sky. The more Lana learned about Jack's financial luck in life, the more, yet again, she couldn't believe that he chose a Goodwill to rob. With so much money to spend, he just about could get away with robbing the queen of England.

As soon as they stepped inside the building, Lana was blown away by the grandness of it all. This is his apartment building? The white marble that coated the floor and walls were sparkly clean, and the space could fit at least ten of her apartment units. They stopped by the concierge and Jack talked to the older gentleman standing by the desk. The man's face lit up when he saw Jack.

"Hey Don, this is my, um, this is Lana. She's just going to hang out here for a second while I run up and grab something for her. Is there water or anything available for her?"

"Why yes, of course, Mr. Hanscom," Don replied warmly. He looked at Lana, smiled, and said, "Nice to meet you, Ms. Lana. What can I get you? Perrier? Tea? Coffee?"

"Oh, thank you! I'm good for now," Lana responded to the sweetest old man in the world.

"Okay, I'll be right back," said Jack, just before he sped away to the elevators.

"Mr. Hanscom is one of our best residents. He always makes sure to get to know any new staff member that is hired. Last year, he bought us all Christmas presents and even helped Rita on the cleaning staff see her family for the holidays. He is truly the best."

Lana smiled genuinely. She looked up at Jack who was still across the room waiting for the elevator. In that instant, she felt like she wanted to know more, to see more. I wonder what it's like in Jack's home.

"It was nice meeting you, Don. I think I'll actually run up real quick with Jack."

Jack's face spelled confusion as he saw Lana heading his way.

"I changed my mind," Lana said as she approached him. "I'm coming up with you. Got to make sure you choose the right box this time."

Jack smiled, and they both walked into the elevator. He tapped on the button for the fourteenth floor and up they went.

***

What are your thoughts on this chapter? Please comment and vote if you're liking the story so far! ♥️