It was decided that a second chance at a date would be the following Friday after everyone had gone home from work. And this time, Stiles had proposed, he would be the one to plan everything. Which, in that moment, had been to avoid any further embarrassment on Stiles's. He felt that if he was more in his element that he wouldn't mess up so much in trying to find a conversation, and therefore wouldn't be so easily ignored. Though, Stiles's figured in his more frantic times of reflection, if something else were to happen that demanded a phone call, then it wasn't like he stood a chance, but Stiles did his best to keep his spirits high and away from such worries.

It helped that throughout the week, whenever they happened to be in the same room together - which happened quite a bit - Derek would sneak him a shy smile. And sometimes when Stiles arrived in the morning it was to see a latte on his desk, the kind he got when he went to the coffee shop with Lydia.

By Wednesday, Erika came up to his desk leaning across the divider in a way that showed off her plentiful assets. Stiles stared straight into her eyes, knowing she positioned herself in such a way to be intimidating. She smirked, "So, you've got yourself a secret admirer?"

He smirked back, though it was much less scary than her's. "Do I?"

"I'm just thinking, you just dumped Malia and suddenly you're receiving lattes on your desks. Seems pretty quick if you ask me."

Stiles's playful demeanor dropped at the mention of Malia. "Well I didn't ask you."

Erika shrugged and pushed herself away from the divider, trying to appear casual, but too cruel to pull it off. "Just thought you should be aware that your ferocious little ex-girlfriend wants to know who this person is, and I'm pretty sure her intentions are less than pure. Not that I can say I blame her."

That day had been a bust, thinking of Malia trying to hunt someone down because she thought that person had stolen him from her. Which was completely untrue, though Stiles could see how it might be seen otherwise. And the moment he started thinking about the situation from another person's perspective, the guilt began to wash over him, worried that he had subconsciously thought to trade up. Though he tried to tell himself that wasn't what he had done; he had just realized that him and Malia weren't right for one another, and there happened to be someone offering themselves up to see if they turned out to be right her stead.

It all sounded bad in his head.

So bad that the thoughts and guilt just kept spinning in Stiles's head until he found himself in an elevator alone with Derek after coming back from lunch. He burned vibrantly at being in such a confined space. Derek, of course, smiled in return. He had his cell in his hand, but promptly pocketed it when Stiles entered. Stiles tried to smile too, once the door had closed, but it must have looked different than his usual smile because Derek cocked his head slightly in question.

"Everything okay?"

In that first second of being asked, Stiles wasn't going to anything. Then, a second after that, he broke down, rambling off his insecurities without taking a breath.

Derek looked at him much like he did that day on the plane when Stiles had gone off in a fear-fueled panic of listing all his secrets. It was a soft look, amused of course, and every so patient. Though this time, when Stiles had finished, gulping in air, it wasn't a smile that graced Derek's features but a small frown.

For an awful moment, Stiles thought his insecurities had ruined what may have started between them, leading him down the mental spiral of convincing himself that if that were true, it was for the best. That they had already tried and failed and there was no real need for a second chance.

The door of the elevator opened.

It was on the floor of Derek's office because Stiles had been too distracted to press the button to take him to where he needed to be. Before he could do so now, Derek stated evenly, "If you wouldn't mind coming up to my office with me. I'd like to discuss the Triskelion file with you."

Unable to decline, Stiles followed the CEO to his office, his insides fluttering and his mind taking off.

The office door was shut behind him the instant they were inside and Derek immediately turned to Stiles, invading the younger man's space. "You shouldn't feel guilty," he stated earnestly and Stiles loved the light that shined in those eyes, struck mute just by the sight of them. "You didn't do anything wrong." Derek moved slightly closer and Stiles found himself backing against the door. "And if it helps to clear your conscience, remember that I asked you out."

"Okay, I'm ready," Stiles announced twirling around the living room. Scott gave a thumbs up, but otherwise looked unimpressed. Indignant to the lack of response, Stiles made a face and placed his hands on his hips before demanding, "Where's the key?"

Scott motioned to the plastic container that had all their loose wires, remotes, and controllers. "Are you sure you want to take him there?" he asked as Stiles pulled out a keyring with a silver crossbow on it, a token Scott had earned while dating Allison that would give him access to an exclusive club downtown.

"Yea," Stiles pocketed the keyring with a crazy grin. "This is going to blow his mind. And will be so much better than some overpressed dinner," he commented as if a side note, making Scott shake his head in amusement. "Plus, clubs are totally my territory so I'll be my lovely self and he won't possibly have a chance to ignore me."

"Since when is clubbing your territory?"

"What? Since Jungle. Come on."

Scott opened his mouth to share his judgments, but then decided against it. He rolled his eyes instead and asked, "What time do you think you'll be back?"

"Why? Do you have a hot date?"

"No," but there was a blush on his cheeks that said otherwise.

"How about I call you when I'm on my way back. That way I don't walk in on you doing the dirty."

Stiles was shooed out of the loft, laughing as the door was shut firmly behind him.

When Stiles reached the coffee shop that they had planned to meet up at it was to the sight of Derek standing in a pair of tight, dark jeans and a black henley with two lattes in hand. He handed one of them to Stiles and then showed him his phone that had been completely turned off. "I told them that if anything came up they would have to call me in the morning."

Stiles grinned happily into the foam of his latte, both pleased about the lack of distraction concerning the phone and about the taste of caramel on his tongue.

"So, I've been meaning to ask. Did I tell you about my drink order? Because I know I talked about the company's awful coffee order, but I don't remember saying anything about what I usually get."

The edges of Derek's eyes crinkled in amusement and a light pink dusted over his cheeks. "No. I just paid attention to what you got when you went out with Lydia."

"Oh, that's sweet," Something within Stiles fluttered and their previous date was long forgotten. "And I mean, a little stalkerish too, but I'm cool with it." He took Derek's in his and began to lead him towards downtown, rambingling about the club he was taking them to. "It's really cool," he was still saying half an hour later when he tugged Derek into an alleyway. "It's like a top secret club that you can't get into without showing a key. And lucky for you, I have that key."

As Stiles continued to ramble, Derek's finger tightened on Stiles's hand. "Are you sure this is the right place?" He was looking around the alleyway suspiciously, the muscles of his forearms bulging as if preparing for a fight."

Heat began to pool together inside Stiles's at the thought of Derek protecting him. Which was something new that Stiles was just now learning about himself. He had never imagined he'd have a damsel in distress kink, but well…. Not that Stiles wouldn't fight back if someone attacked them, but it was a nice thought. A nice, sexy thought. It was certainly something to keep him occupied during the night when he was alone.

"Yea, I'm sure this is the place," Stiles shook the images away to lead them confidently to a dark blue door. "I told you, it's top secret, so of course it's going to be hidden where most people wouldn't change upon it."

Derek didn't look convinced, but he continued to keep in step with Stiles's stride and nothing more about his reservations.

Stiles let go of Derek's hand momentarily so he could rap his knuckles against the door and pull out the key ring. Anticipation had him bouncing on the balls of his feet. Derek was going to be so impressed, he thought gleefully. And it was going to be so much better than some fancy smancy dinner.

But when minutes passed by and no one answered, his antsy behavior began to take a more nervous edge. "I know this is the place," he said aloud, as if to convince more than just Derek. He sighed in relief when someone finally cracked open the door after the third knock. Proudly, Stiles displayed the key ring.

The man peered through the crack, the door restricted by chain, and looked curiously at the key ring before starting at Stiles blankly. "Is there something you wanted?"

Stiles floundered and tried to stutter his way through an explanation, having thought that the key itself would be enough to get them in, but from the raised eyebrow Derek was giving him off from the side said that he wasn't doing a good job of it.

The man on the other side of the door just looked him up and down oddly. "Look," he stopped Stiles from continuing his nonsense mutterings, "if you're looking for something to take the edge off or whatever, come inside. I'm sure we can arrange something for you."

"Uh," Stiles took a step back as the man began to close the door and unhook the latch, half of his brain realizing what the man meant and the other half of him wanting to deny that this was actually happening.

Derek had a strong arm around him instantly, guiding him away from the blue door. "No thank you. We're good," and then forcibly led Stiles out of the alleyway, his entire side pressed against him like a shield.

Stiles was mortified. He had been so sure that he had the right place - was still sure - and he became deflated with shame and embarrassment. His entire face was red, as well as his ears and chest. With his head hung low, he dragged his feet alongside Derek. "They must have shut down," he spoke quietly, barely above a whisper, "Scott and I used to go plenty of times with his girlfriend but she moved to France and we hadn't had a reason to come back. I'm so sorry I ruined our date. Man, I should have checked beforehand, but I just thought…"

"It's okay. Nothing's ruined." Beautiful eyes met Stiles's with a laughing gleam to them. It only made Stiles blush even more, oddly pleased that no matter he seemed to do, Derek's ration always seemed to be one of amusement.

"So, do you think you could be up for some pizza then?" Stiles asked shyly, eyeing the Chicago Pizzeria across from them. "I know it isn't anything fancy like what you had planned or as fun as what I had planned but mean…"

Derek lightly squeezed Stiles's hand. "Pizza sounds great."