A/N: I only own the story. And sorry for the short chapters. I'm going to do what I can to make them longer after this. I just like breaking it off at a point that provides a good pause. And as always, thoughts are appreciated, as are comments.

"So what do you have planned for us today, Astrid?" Hiccup inquired while putting together two plates of lasagna and mixed vegetables.

"Oh, nothing much. Maybe going to a park, maybe getting coffee, but mostly finding you a boyfriend," Astrid delivered smoothly and quite conversationally, as if she hadn't dropped the 'boyfriend' bomb.

Hiccup, who had just been about to place the plates in the heating oven, nearly dropped the food he was holding as he quickly spun around and reactionally yelped, "WHAT?!" The spin almost sent him tripping backwards into the open oven, but luckily he saved himself before meeting his fiery doom. "Astrid, where the HELL did that come from?"

"Technically my mouth."

"Thanks. Exactly what I meant."

"Hiccup you're going to be a Junior in college and you haven't even tried dating anyone yet."

"What, is that so wrong? I'm busy with classes, I have no free time, and yes I actually have tried dating people before, I just haven't told anyone about it! And anyways, it's not like I'm lonely. I have Toothless!" Hiccup said this with arms waving wide, nearly sending the food flying from the plates still in his hands. Upon his mention and gesture towards Toothless, the cat briefly glanced up at his human with a look of 'Why are you speaking of me?'

"Uh huh. Sure," Astrid delivered with a disbelieving face. "And no, you haven't dated. Not only would you have told me or at least made hints towards your date, but your current blush gives away your lie."

Hiccup blushed harder and looked down. Although he was actually telling the truth about dating, he knew it wasn't worth getting into. The blush was from his embarrassment of even talking about this past and his lie of not being lonely.

"That, and I stole your phone while you showered."

"Astrid!"

"You haven't been texting anyone you don't know, you don't have snapchat, you have no history of downloading Tinder or Grindr, and Gods do we know that you wouldn't go clubbing alone," the madwoman listed with nonchalance. "Though I am glad you don't go out alone. Drinking alone is just sad and flying solo is unsafe."

Hiccup was absolutely speechless, his mouth agape with astonishment. He let out a slight cough, "Well. You certainly covered all your bases, didn't you?"

"Yes I did," Astrid said with more than a hint of smugness.

"So what now? Are you going to open one of my closets and reveal the 10 suitors you brought with you?" Hiccup shot back sarcastically.

"No, I'm going to take you speed dating, you doofus."

"WHAT!"

"HA! I knew that would get you."

"Jerk."

"Although that would have been fun to watch you flounder in a forced social interaction, I actually want you to get somewhere and we both know you're too awkward to take on speed dating or picking up dates in a bar by yourself. And let's be honest. Most people you pick up at the bar tend to just want into your pants, not your life."

"You have a point there," he conceded. "But if I tried I could meet someone in public!"

"Oh yeah?

"Yeah! It's just that it's so hard to tell who's gay or bi or whatever and who's straight. There is no such thing as a gaydar Astrid," Hiccup stated while finally placing the plates in the oven. "As useful as it would be, it just doesn't exist. And I don't want to accidentally hit on some straight dude. They might… you know… not take it well."

"Aah. Yeah. That makes sense," Astrid agreed thoughtfully.

"Mmhmm."

"So that's why I thought you should download Grindr."

"NO!" Hiccup shouted. Gods I'm shouting a lot… Oh well. Astrid's fault. He cleared his throat. "No," He said more calmly," It's not a good place to look."

"What do you mean? It's just a dating app. And how would you know? You haven't downloaded it! I checked."

"Yeah, just a dating app where gross old men hit on you 24/7 even when your profile says you're not interested. They just are so entitled and think they're an exception so they go ahead and talk to you anyways and then when that doesn't work they send pictures of their gross dick. It's just not okay Astrid. I tried once on my old phone. Never again." Hiccup stated forcefully and with finality. His face fell for the briefest of seconds, a hurt expression taking over, giving away a moment of pained reflection before it returned to his usual 'natural' façade.

"Wait, Hiccup, what's wrong?" Astrid asked with genuine concern.

Hiccup, now fully realizing his front fell, gathered himself and said, "Don't worry about it Astrid. I'm not going to talk about it anyways."

"Hiccup, don't just brush me off like that. I – "

"Astrid!" Hiccup cut in sternly, "I'm not going to talk about it. Drop it."

She huffed and took the worried look off her face, "Okay, Hiccup. I'm just worried about you. You're my best friend."

"It's alright Astrid. I just don't like bringing those memories up… Anyways, you're right," Hiccup said in a more uplifting tone, "I should try to get back out there. Try dating again."

A huge grin broke out across Astrid's face, "Wait, really?! I thought for sure I would have to bribe you or blackmail you or something! This is so much easier."

"Wait, blackmail? What do you mean blackmail Astrid? What do you have on me. And wait a second, you never answered me when I asked how you got in!"

"Well if I told you what it was then I'd never be able to use it on you. So no," Astrid grinned darkly, "And I know where you hide your key, Hiccup. I am your best friend after all."

"And all best friends fully intend on blackmailing each other. Sounds totally legitimate."

"But am I wrong?"

Hiccup paused for a second. "Well… Not really I guess," he said thoughtfully. And of course she knew where I hid my keys… I have to find a better spot for those. Maybe behind some fake mortar on the brick wall…

Astrid spoke, breaking Hiccup from his reverie. "So how do you want to do this? Although we already covered how bar dudes usually just want a joy-ride, I feel like it's at least worth a shot. And anyways, gay bars just tend to be fun! Or we can just download Tinder, that's always an option."

Hiccup made his way to the rocking chair opposite of the couch Astrid was laying on, thinking quickly. "Well, I guess I don't mind giving the bar a shot. It gives us something to do tonight and I would honestly prefer meeting people, you know, in person," he explained with multiple sweeping arm movements that most people would find unnecessary but that Astrid was completely used to by now.

"Fantastic! I was hoping you'd say that. Now I can get you drunk too! This just keeps getting better and better."

"You're evil, Astrid."

"And you love me for it, don't you Hiccup?"

A timer dinged in the kitchen and Hiccup stood up before saying in the driest, most sarcastic tone that he had, "More than anything else in the world."

"You're an ass," Astrid shot back without pause.

Hiccup smirked, "And you love me for it, don't you Astrid?" Nailed it.