A/N: I'm so glad so many of you enjoyed the last chapter! I hope you enjoy this one too ?

Disclaimer: I own nothing.

Chapter 11: Dating Problems

The next day was a Friday, which Ana was simultaneously thankful for and also deeply dreading. Her conversation with Christian last night was still occupying her mind, and it had caused her to stay up late into the night while mentally mulling over every word he said, every inflection in his voice, and every expression on his face. She woke up early Friday morning feeling both mentally and physically exhausted.

One thing she felt she couldn't deny anymore was that Christian was definitely flirting with her. She had suspected his flirtation with her at several points in the past, but she always brushed it off as him just messing with her. Now, however, he essentially confirmed that he enjoyed trying to rile her up. That he liked seeing how she reacted, and she, as he put it, 'fascinated' him.

The angry look you get on your face, the flush that comes over your skin… even the snappy retorts that come out of your smart mouth. It fascinates me.

Ana felt her heart race as she recalled his words to her last night. Could it be that Christian was actually attracted to her? Or was this just a new way he was trying to screw with her? Ana couldn't seem to settle on one conclusion, so when she finally went into work Friday morning, she was still struggling with a whole plethora of conflicting emotions.

Ana now walked toward her and Christian's shared office, noticing through the glass wall Christian already sitting at his desk. However, someone else was also in the office – the intern, Jack Hyde, was standing there, holding a clipboard in his hand.

Wondering what was going on, Ana opened the door, and both men looked over. "Good morning," Ana said, looking curiously at Jack. "Hi Jack, how are you?"

"'Morning Ana," Jack smiled back at her. "I'm doing well, thank you. I have a question for you though – I've been going around to all the marketing agents this morning to see if they can help me."

"Sure. What's up?" Ana said kindly, moving behind her desk and setting her purse down.

"I'm doing a project for my Marketing & Communications class," he explained, walking over to Ana's desk. "It's a part of this summer internship program I'm doing here at Kavanaugh Media. I need to make a presentation explaining how a marketing plan works, and I would like to show some real-world examples. Would you be willing to share with me the marketing plan of one of your clients that I could use in my presentation?"

"Of course," Ana said, but then a thought occurred to her. "Max knows about this, right? Because there might be some confidentiality issues when it comes to our clients. I don't want you to get in trouble…"

"Max knows about the project, and he's already signed off on it," Jack assured her quickly. "I'm not going to use the clients' names in my presentation, so there shouldn't be any breaches of confidentiality."

"Okay, that's good," Ana smiled. "I can send you the marketing plan of my client ProTech Medical. They manufacture medical devices, and I think theirs is a good template for a lot of the marketing plans we create here at Kavanaugh Media."

"Awesome. Thank you so much," Jack said gratefully, jotting down a note on his clipboard. "And Christian, you'll send me the marketing plan for Foster Polymers?"

"Yup," Christian said, smiling at him. "Is there anything else you needed?"

"Nope, that should be it," Jack said, smiling at him and Ana. "Thank you guys so much. I really appreciate this."

"No problem," Ana said kindly.

"Happy to help," Christian nodded.

Jack left, and Christian and Ana both glanced at each other. Ana felt her heart stutter slightly in her chest, realizing the two of them were alone now, but Christian didn't seem to notice her anxiousness as he smirked.

"That definitely doesn't make me miss being in school," he noted with humor, turning back to his computer. "All those projects and presentations I had to do were brutal."

Ana blinked before smiling, seeing an opportunity to rib him. "Oh please. I'm sure a rich boy like you did just fine in school," she said sarcastically, finally taking a seat behind her desk.

"Of course," Christian rolled his eyes. "I couldn't possibly know what hard work feels like because my daddy is rich, right?"

"Exactly. It's good to see you embracing your true self," Ana said with mock encouragement. Christian let out a snort.

"You clearly don't need any help embracing your true self, now do you?" he said, his implication clear as he raised an eyebrow at her.

Ana giggled, feeling weirdly comforted at the fact that the two of them were able to fall back into their usual snarky back-and-forths, even after their heavy conversation last night. "Apparently not," she said glibly, turning to her own computer and powering it on.

~/~

Later that morning, Ana received a Slack message from Nadia asking to meet her and Jessica in the break room ASAP. Ana had a couple emails she needed to fire off to clients beforehand, so she didn't get up from her desk until about ten minutes later. When she finally walked into the break room, Nadia and Jessica were both there waiting for her.

"There you are," Nadia smiled when she saw Ana walk in. "Sorry if you were busy, but we didn't want to go to your office in case Max was hanging around."

"Why? What's going on?" Ana asked curiously. Jessica handed Ana a brochure, smiling eagerly, and Ana took it, frowning.

"'The Single Hop'," she read the title on the front out loud, and she opened the brochure to read what was inside. Her stomach flipped when she realized what this was. "Oh no, guys. I don't think this is a good idea…"

"It's a speed-dating event happening tonight," Nadia explained, looking excited. "And it's at a bar only a few blocks away from here! Jessica and I thought this could be kind of fun and different for our official girls' night out."

"I don't know," Ana said skeptically, shaking her head as she continued to glance over the brochure. "First of all, Nadia, you have a boyfriend. And second of all, I thought we wanted to go clubbing together?"

"We can still do that another night," Jessica said fairly. "But this speed dating event is going on for just one night. Why don't we go tonight after work and see what it's like?"

"Yeah. And Michael already knows about this," Nadia piped up. "I always tell him everything. He knows I'm just going to support my two single besties."

"I've always wanted to try speed dating," Jessica said to Ana, giving her an imploring look. "Nadia and I figured since you and Jose just broke up, this'll be the perfect opportunity for you to put yourself back out there."

"But if you feel like it's too soon, we understand," Nadia said quickly. "We just thought we could try it. And if we all end up hating it, we can just leave and go bar-hopping together for a bit."

Ana grinned reluctantly, finally starting to warm up to the idea if it meant she could spend some more time with her friends. "Alright. If it means that much to you guys, I guess I can give speed-dating a shot. All I ask is that bar-hopping afterward is mandatory."

Nadia and Jessica both smiled brightly, looking happy to have convinced her. "Yay! And yes – we're all definitely doing drinks afterward," Jessica laughed, clapping her hands together. "I can't wait!"

Ana smiled back, starting to feel a little excited for tonight too. Speed-dating may not have been something she initially thought she would want to do, but after everything that went down with Jose earlier in the week, this actually might be a fun way to get back into the dating game.

Was she ready, though? Could she really try to put herself out there and feel a spark with someone once again?

For some reason, the thought of Christian standing in her kitchen last night popped into her mind, a certain expression crossing over his face as he gazed at her, making her pulse pound and her face blush…

Ana quickly shook her head, trying to push those thoughts away. She wasn't sure why her mind went to Christian, and she didn't really want to dwell on it.

~/~

The rest of Ana's day went by normally enough. She'd had a few meetings and phone calls with clients, but even as she dived into her work, she couldn't keep her mind off of speed-dating later tonight. It was going to start at seven o'clock, but she, Nadia, and Jessica had agreed to grab a bite to eat somewhere beforehand.

As the end of the work day drew nearer, Ana began to feel more nervous for what was about to happen, and she couldn't help but keep glancing at the clock as it ticked closer to when she would leave.

"Desperate to get out of here, are we Steele?" Christian now asked, clearly noticing Ana continuously glancing at the wall clock.

"What? Oh. Yeah, I s'pose," Ana said, biting her lip as she glanced at the clock again. "Nadia, Jessica, and I are going out for drinks after work tonight."

It was a half-truth. She sure as hell was not going to mention speed-dating to Christian since he would undoubtedly mock her relentlessly for it.

"Really? That sounds like fun," Christian said, nodding. "I assume your girls' night out will consist of margaritas, drunk karaoke, and sticking your heads out of limousine windows while yelling 'whoo!'."

Ana couldn't help smirk in amusement. "Oh, definitely. And don't forget our margaritas need penis-shaped crazy straws."

Christian laughed. "Obviously."

At that moment, Ana saw through the glass wall Nadia and Jessica approach her office, both of them with their coats and purses in hand. Before Ana could step out and join them, Nadia walked up and opened their door, peeking her head inside.

"Hey Ana! Ready to go?" she asked brightly. She and Jessica stepped inside. "Hi Christian."

"Hello, ladies," Christian greeted them politely.

Ana suddenly felt a sense of dread fill her body: she realized Jessica and Nadia could very well let it slip to Christian right now that they were going speed-dating tonight.

Shit, we need to get out of here.

"Yup, I'm ready. We can go right now," Ana said, quickly powering down her computer and hopping to her feet.

"So what bar are you guys going to?" Christian asked Nadia and Jessica in a conversational tone. Ana felt her anxiety shoot up, and she spoke up before her friends could:

"Um, we don't know yet," she said, gathering up her things. "Let's get going, guys."

"Well, Nadia and I were thinking we could all grab dinner at City Street Grille before we head over to The Single Hop," Jessica said, glancing between Nadia and Ana. "What do you think?"

"Sounds good," Ana said quickly, pulling on her coat and walking toward them.

"What's The Single Hop? Is it a bar?" Christian asked curiously, and Ana felt herself begin to panic.

"It's a speed-dating event happening tonight," Jessica smiled at Christian, clearly not noticing Ana's distress. "The three of us thought it would be fun to try it out."

Christian's eyebrows raised, and his eyes seemed to light up as he slowly turned to look at Ana. There was a certain gleam to his expression Ana didn't like. "…Oh really?" he asked, a restrained delight in his voice.

Ana closed her eyes, silently cursing her friend and her inability to read minds. "It wasn't my idea, alright?"

"Jess and I figured since Ana's newly single, this could be a fun way for her to get herself out there again," Nadia explained, grinning over at Ana. "She was kind of reluctant, but we twisted her arm in the end."

"Of course," Christian smirked, leaning back in his chair as he observed Ana, still with that same gleam in his eye. "Well, I think speed-dating sounds like a great idea. I've never done it, of course, but I hear it's a lot of fun."

Ana narrowed her eyes at him, wishing more than ever she could smack that smug look off his face. "How was your date with Kate Kavanaugh, by the way? I don't think I ever asked."

Christian's smile dropped slightly as he raised an eyebrow at her. "There wasn't really a connection. But I'm sure I don't need to tell you."

Ana and Christian continued to stare at each other: or rather, Ana tried staring him down while Christian refused to look away.

"Yeah, I think we all kind of knew Kate's a bit crazy," Jessica snickered. "I'm sorry your date with her didn't go well, Christian, but you're welcome to come speed-dating with us tonight."

Ana whipped around to stare at Jessica with wide eyes. "What? No."

Jessica looked unbothered, however, as she shrugged. "What? If he's single too, then he might have fun speed-dating with us."

"He did say he'd never done it before," Nadia piped up, glancing over at Christian. "C'mon, Christian – what do you say? Would you like to join us tonight?"

Ana looked back at Christian, who was still staring directly at her. His expression was unreadable, but after a moment he grinned.

"You know what? Why not?" he said brightly, turning to look at Jessica and Nadia. "I don't have anything going on tonight. What time is it at?"

Ana clenched her jaw before closing her eyes, whatever enthusiasm she had for the evening evaporating in an instant.

A/N: Hm, this should be interesting ;)

Please review! Next chapter, Ana and Christian go speed-dating.