Description: In which Allison tried to play matchmaker and set her best friend up with her brother.

(Don't have a playlist for this one because I literally based this on When He Sees Me from Waitress the Musical. Please go listen to it, PLEASE)


"Remind me, which one of your siblings am I meeting again?"

You asked, anxiously studying your reflection in the mirror as your friend looks through your closet. "Diego. Knife boy? Does that ring a bell? No?" Allison sighed and put down the jacket she was holding up, "I know that I somehow forced you into this but at least try to remember your date's name?"

"I'm sorry, I'm just so nervous." you said apologetically. This was a bad idea, you knew it. You shouldn't have agreed on going on a blind date with Allison's brother in the first place and now it was too late to back out. She made it sound like such a good idea at that time. You were really really single, hadn't gone out with anyone since you broke up with your ex and he was getting over a heartbreak, equally single as you were. You kept trying to tell yourself that nothing could go wrong, just think of it as a casual night out, you could at least have some fun even if you ended up not hitting it off with the man.

But another part of your mind was just screaming at you to get yourself out of this before you do anything you might regret.

"Are you sure about this?" you turned to look at Allison after giving up on making your hair look any more presentable. She gave you a confused look, "What do you mean am I sure?"

"I mean," you sighed, "what if we really don't get along? Like, 'getting annoyed with each other immediately' not get along. Maybe he does not even want to meet someone new in the first place and we just sat there in complete silence for hours and like-"

"Whoa, whoa, whoa, whoa," Allison walked over and grabbed your shoulders, "calm down." You took a deep breath and she let go of your arms, "You were still looking forward to it when we talked about it yesterday and now you're full on panicking. Did something happened? Did someone said anything to you? Who do I need to talk to?"

"No, it wasn't that." You stopped your friend before she could make any more assumptions. "I just... I don't know... I have no idea what he is like but then I'm literally spending the entire night with him and so many things could go wrong! You know, blind dating can be very dangerous."

"Can't argue with that but you do remember that Diego is my brother right?" Allison said with her eyebrow raised, now looking at you with a hint of amusement.

"Adopted."

"That too but we still grew up together," she said, "besides, I won't just set you up with someone who is any less than trustworthy. You're my closest friend for god's sake and I care for you, a lot." You groaned and turned back to the mirror to fix your hair for what felt like the hundredth time.

"It's going to be fine, I promise!" Allison said, trying her best to sound excited, "And stop messing with your hair, it looks great already and you're not doing anything ruffling it like that."

"Please tell me you're not wearing this." Klaus said in horror as he passed by his brother's room and saw him in his usual clothes, that same black shirt with that damn harness, "You're going on a date! At least pretend like you've tried. I mean, the chance to meet someone who is into bondage is so much higher nowadays but still!"

"It's not anything special," Diego said and went out of his room, "It's just a blind date that Allison forced me to go on. What's the point in dressing up for something I didn't even sign up for?"

"But, but, but," Klaus ran out and blocked his way, earning a glare from his brother, "imagine how hurt that person would be if you so obviouslt don't give a damn? At this point, you might as well have 'I don't want to be here' carved onto your forehead. Come on! Go change into something nicer, at least take off the harness."

Letting out an annoyed huff, Diego turned back and started unstrapping the leather belts. "Why are you so pissed about this?" Klaus sat on his bed with his legs crossed, "You haven't gone out and have fun in a long while, I don't see the harm in this."

"Because I don't want to?" Diego said almost matter-of-factly, "Allison is trying to set me up with one of her friends and knowing her social circle, they are probably one of those flashy attention seekers that got close with her to get famous. I'm not even sure if that is actually her friend or just someone who doesn't mind hopping from date to date."

Klaus smirked and let out a dry laugh, "Look at you making assumptions before even meeting the person. Do you know anything about your date?"

"Apparently, they were one of the writers for the last film she was in. They offered to help babysit Clare once when sis was having a press release which was how they got close in the first place." Diego paused for a second and added, "And they make a banging lasagna, although I don't see the point in her telling me that. It is not even a proper date."

"A writer huh? Doesn't sound that bad. Maybe they would be interested in whatever the hell you do, you know how writers tend to like the weirdest things."

"Ha, ha. Very funny Klaus." Diego rolled his eyes, "I'm telling you, I'm only doing this because Allison is such a bother when she insists on something."

"Whatever you say," Klaus threw his hands up in the air as a sign of surrender, "but you really need to consider you clothing options. Oh! I can borrow you one of my shirts! No? Ok."

"You're gonna like him, I assure you." Allison held your hands. You had 20 minutes before you leave your house and you had not felt so nervous since you handed your last script to a director.

"And if I don't?"

"Then it is his fault for not impressing you enough to like him."

"What if he doesn't like what me enough to want to impress me?"

"Then he's missing out because you are way too good for him anyways."

You gave her a small smile. Sometimes you wonder how you were so lucky to have such an amazing person in your life. "You know what scares me the most?" you said softly, finally gaining enough courage to tell her what was truly bothering you, "What if when he sees me, I really like him and he knows it?"

Allison did not know how to respond to what you just said and you carried on, "What am I suppose to do when that happens? I'm not prepared to open up my life to someone new, I'm scared that it would only leave me heartbroken once again. What should I do then?"

"Oh, (y/n)..." Allison walked over and pulled you into a tight hug, "Thank you for opening up to me. I'm sorry that I haven't thought of this in the first place. Diego can be an assholes sometimes but he is a softie deep inside and I'm sure that he won't do anything to hurt you." She pulled back and felt a lot more relieved when she saw your smile, "And if he does, brother or not I will skin him alive."

"Damn, girl. Aren't you aggressive?" you gave her a grin which earned you a smack on the arm. Checking the wall clock, you got up as you saw the time, "I should go, wouldn't want to be late on a date.

"Now that's the attitude I was looking for!"

"Why are you so defensive?" Klaus yelled, beyond frustrated after Diego once again refused to get out of his usual patrolling outfit.

"I'm not defensive!" Diego said, emphasizing on the second word. "I'm just annoyed that I am doing this stupid thing when there are other ways I can spend my time instead!"

"Like what?" Klaus groaned, "Why are you dismissing the possibility that you might actually meet a nice person and have a good time?"

"Because no good person in their right mind would want to be stuck with me!" Diego yelled back, "Hell! I might be meeting the most amazing person on earth but why should that matter when I'm just gonna ruin them like I ruin everyone that came before?" His outrage left Klaus at shook. He had guessed that his brother was still deeply insecure and doubtful of his own lifestyle and felt guilty after what happened to Patch but not anything like this. Having a pretty messed up life himself, Klaus was never the best at comforting people but there was nothing he could do but try when his brother was so visibly vulnerable.

"But that wasn't your fault," Klaus said softly with his hand on Diego's back, "you can't keep on letting that holding you back from ever being happy again, you know?"

Diego sighed, "Maybe you're right. But I'm not even sure if I can still fall in love with someone after all that."

Klaus pulled him in for a hug. It was strange for the both of them, seeing as they didn't have the most intimate relationship but Diego appreciated his effort nevertheless.

"So which shirt should I wear, again?"

"Finally you're listening! I feel like I was about to lose my mind."

You stood outside the restaurant, nervously checking the time on your phone. At this point, you weren't even sure if being early is a good thing or not. You felt your heart pounding harder everytime the minutes of the clock moved. Thoughts on the probabily of getting ditched even before knowing who you were seeing was about to start messing with your mind when you heard a deep voice calling out for you.

"Hey, uh, you're (y/n) right? Sorry that my sister dragged you into this, she was very keen on getting me to go out with someone."

You looked up and found yourself in front of this beautiful man. Realizing that staring at someone without saying anything might be a bit creepy, you reached out and gave him a quick handshake along the lines of brief self-introduction.

Taking a better look at your date, you noticed that he was rather well-built.

"Nice shirt."

"Thanks, my brother forced me to wear it, said that it compliments my frame, whatever that means." he scratched the back of his head in embarrassment and smiled. Damn, that smile.

"Should we go in?" he said, realizing that you two had been standing out there for an oddly long time and you hummed in response. Giving him an appreciative nod as he held the door for you, you thought to yourself "Ok, maybe this isn't as bad as I thought it would be."

Bonus

(You have 3 new messages)

-how was the date?

-Diego?

-?

Good morning to you too sis

-so how was it

-and what do you mean 'good morning' it is noon

well

I was tired after getting to know your friend last night;)

-DIEGO