Identity Risk (The Billionaire Experience #3)

Chapter Five

Jessie sat in the plush, modern conference room of “One and Done.” She felt out of place and more than a little embarrassed. She adjusted her blazer, trying to ignore the growing knot in her stomach while waiting for Ana Serrano, the app’s designer, to join her.

A few anxious minutes later, the door opened, and a tall woman with a confident stride and a warm smile walked in. Jessie assumed this was Ana. She was every bit as poised as Jessie had imagined. Her sleek black dress and stylish glasses added to her air of professionalism. She carried herself with the confidence of a queen.

“Jessie, it’s a pleasure to meet you. I’m Ana Serrano,” the woman said, extending her hand.

Jessie stood and shook her hand, managing a polite smile. “Nice to meet you too, Ana. Though I must admit, I’m still not sure I should be here.”

Ana laughed lightly as she took a seat across from Jessie and opened a folder. “I hear that a lot. It’s not every day your best friend signs you up for something like this.”

Jessie’s cheeks flushed. “Exactly. I’m a little embarrassed, to be honest. This whole thing feels…well, a bit surreal, and not something I would normally do.”

Ana nodded understandingly. “I get it. But I assure you, it’s more fun than it initially seems. Let me explain how it works, and you might feel better about it. But before I do that, I must tell you that your profile has garnered quite a bit of interest already.”

Jessie’s eyes widened. “Seriously?”

Ana smiled. “Yes. You see, normally, our billionaires are male. So, having a female is rare, and men are jumping at the opportunity to win your time.”

Jessie swallowed hard. Jesus, she was going to kill Lacie for getting her involved in this.

She leaned back in the chair, nodding for Ana to continue.

“So,” Ana began, “the way ‘One and Done’ works is pretty simple. As the billionaire—”

Jessie cringed slightly at the word, but Ana continued without missing a beat.

“—you get to set your preferences in terms of looks, personality traits, and any specific likes you have. On the other side, the non-billionaire participant shares a dream date they’ve always wanted to go on. It’s meant to be a once-in-a-lifetime experience for them.”

Jessie raised an eyebrow. “So, I’ll pick a date based on a fantasy they’ve created?”

“Exactly,” Ana confirmed. “You’ll be presented with a few options that fit the criteria you set. You choose the date you’re willing to pay for and attend. Once you’ve made your choice, the selected participant will be given a description of you—nothing too personal, just enough for them to decide if they’re comfortable.”

Jessie nodded slowly, trying to wrap her head around the concept. “And there’s no money exchanged? And I don’t have to share my real name or occupation?”

“Absolutely not. It’s meant to be an escape,” Ana said gently. “A chance to step out of your life for a night and enjoy something without the complications of the real world.”

“Does sex have to be involved?” Jessie blurted out, deciding to get the question she had been dying to ask out of the way.

“Nope. Whatever happens during the date is up to you and the other party. I will tell you that each participant is fully vetted, and a background check is completed.”

Jessie nodded and sighed, her thoughts racing. “I don’t know. It just feels like I’m buying someone’s time.”

Ana leaned forward. Her expression was understanding. “Think of it as creating a memory for someone—one that they’ll treasure forever. And you get to share that memory without any expectations or obligations afterward. That is the one rule. There is no contact again after the date is over. You will each sign an NDA.”

Jessie thought about it for a moment, then gave a small nod. “Okay, I’ll give it a shot. But I’m still a little nervous.”

Ana smiled warmly. “That’s perfectly normal. Just remember, this is supposed to be fun. Who knows? You might end up with a story you’ll be glad you said yes to.”

Oh, Jessie was sure that there would be a story involved, and it may end with the murder of her best friend.

Jessie spent a few more minutes going over information about the app and how it worked. Ana briefly showed her the list of men who were already matched to her. She swallowed hard. How was she supposed to choose just one?

As Jessie left Ana’s office and walked back to her office, her thoughts were a jumble of excitement and uncertainty. This was definitely not how she imagined stepping back into the world, but maybe, just maybe, it could be the adventure she didn’t know she needed.

She was going to need Lacie’s help in narrowing down her matches. She wanted to do it quickly to get it all over with.

◆◆◆

Jessie walked into her office with a pizza she picked up on the way back to the office. She set it down on the table in front of the sofa on the other side of the room. She sat down, opened her laptop, and brought up the dating app. She was glad she could scroll through the profiles on the computer instead of just her phone.

Lacie walked in a few minutes later. Jessie smirked, taking in Lacie’s bare feet.

“God, that pizza smells so good. I’m starving,” Lacie said, plopping down beside Jessie and helping herself to a slice of veggie-covered pizza.

“So, are you ready to pick your boy toy?” Lacie asked, her voice full of amusement.

“Funny,” Jessie replied before setting the laptop on the table in the middle so they both could see.

They started scrolling through the profiles.

Lacie laughed, pointing to one of the profiles on the screen. “Well, here’s a charmer,” Lacie said, her voice full of sarcasm as she clicked on the full profile. “He wants a true fantasy experience.” She raised an eyebrow, smirking. “Involves some kinky stuff. Like role play and other things,” Lacie said, her face turning red as she moved to the next profile.

Jessie chuckled, shaking her head. “Well, at least he’s honest about what he’s looking for.”

As the profiles continued to flash on the screen, Jessie found herself sinking deeper into her thoughts. The whole blind date thing still didn’t sit right with her. She couldn’t shake the lingering memories of Mac. It was hard enough seeing the pictures of him at events with beautiful women. Before she disappeared, he had been her everything—her rock, her safe place, someone she could confide in. The idea of going on a date with a complete stranger, even if it was just one night, made her feel like she was betraying that love she still held onto. Maybe she should try reaching out to him.

“I don’t know about this,” Jessie murmured, more to herself than to Lacie. She was already getting cold feet.

Lacie nudged her shoulder playfully. “You’re overthinking it. Just relax and have fun. It’s one night, and remember Ana said you don’t have to have sex. Plus, you never know. It might be exactly what you need.”

Jessie sighed, dragging her eyes back to the screen. She wasn’t so sure.

As they continued scrolling through a few more profiles. Some were grand fantasies of more than one night of exotic trips, and others just didn’t feel right.

But then, a highlighted profile caught her eye.

“Wait, go back to that one,” Jessie told Lacie, pointing to the screen and profile that was highlighted in gold.

Jessie’s gaze focused on the profile. The man wasn’t asking for much—no wild fantasy, no outrageous demands. His ideal date was simple: sailing around the Hudson River at sunset, enjoying the evening breeze and the views of the city and the sunset. The idea sounded peaceful and romantic. It tugged something deep inside her.

“Oh! According to his profile, sex is negotiable,” Jessie noted, scanning through the rest of the profile, wanting more information on the stranger. “Just someone to spend a romantic evening with,” she said, stating what was shown on the guy’s profile.

Lacie leaned in, reading it. “He sounds like a gentleman. I mean, how many guys would pass up an opportunity like this without trying to push for something more?”

Jessie bit her lip as she read on. The man described himself briefly as being over six feet tall, having dark hair, loved to work out, and enjoyed cooking. He said he had a stable job but didn’t specify what it was.

“It’s a little vague,” Jessie said quietly. But the more she read, the more intrigued she became. There was a certain mystery to him, and that appealed to her. There was no mention of wealth or status, just a man looking for a quiet, romantic evening.

Lacie glanced at Jessie and raised her eyebrows. “What do you think? He seems like a decent option. I think it is right up your alley.”

Jessie hesitated. Something about the man’s profile pulled at her, and she wasn’t sure if it was the simplicity of his ideal date or the way he didn’t seem to be after anything more than a shared moment. It felt familiar but, at the same time, different from the others. “I like it,” she admitted, almost surprised by her own words.

“Then why not choose him?” Lacie encouraged.

Jessie’s heart fluttered, torn between the ghost of Mac and the idea of moving forward, even if just for one evening. She took a deep breath, then clicked accept on Matt’s profile. God, that probably wasn’t even his real name.

“Okay,” she said softly. “Let’s see what happens.”

Lacie wrapped an arm around her, giving her a half hug.

“I’m proud of you, Jess. And again, just try to enjoy yourself and let whatever happens happen.”

Easier said than done. Jessie thought to herself.