When Fishlegs asks Hiccup to be his wingman for a date with Heather, he is totally against the idea, but when he finds out that his high school crush is going to be there things take a different turn to what he was expecting [Modern AU] [Hiccstrid]

When Hiccup agreed to meet Fishlegs for a coffee in Berk's only Starbuck's he thought it would be the usual, play a game of 'Maces and Talons' and have a couple of coffees over the game, boy was he wrong.

"Fishlegs, the last time I've seen you this nervous was when you got married to Ruffnut in a school play and had to kiss her. In fact, I still have the video of when you fainted during the play, when you were meant to kiss her." I said with a laugh at that memory.

"Nervous me? I'm not nervous at all." Replied Fishlegs, as they both ordered are usual drinks; Fishlegs a hot chocolate and myself a latte.

"So, what's the problem this time? Parents are coming around? Family party? Meatlug gone to the vets again?" Meatlug, was Fishlegs' dog, a large sausage dog to be precise.

"Parents were here last weekend and no thanks for your concern but now that Meatlug is on a strict diet and getting plenty of walks, she's fine. How's Toothless?" asked Fishlegs.

"Oh, he's fine. He hasn't lost any more legs. If that's what you were wondering." Toothless, was my three-legged cat, he lost his left leg in a car crash and I found him in a cat shelter and took him in, we've been inseparable ever since. "Anyway, stop trying to change the subject what the problem?"

After a period of silence, I asked again, "Fishy, what's the matter?"

"I've got a date" said Fishlegs.

"So, let me get this straight, you've got a date?" I asked. "Well congrats, good for you mate."

We then moved on to are usual table, by the window, over-looking the town. From here you could see all of Berk, including the Town Hall, where my Dad spent most of his time, due to being the Mayor of Berk.

"So, who is the lucky lady to have a date with the mighty Fishlegs?" We set out the board for the start of the game and it was my turn to go first.

"Heather." Was the reply from my friend.

"Heather, as in Dagur's younger sister?" Dagur, was a strange man and for some reason called me his 'brother', but, he was a family friend and a well-known person across the archipelago. He was the son, of the mayor of Berserk, a near by city. Me and him go long-back to when we were just kids messing around at the annual meetings between the two mayors.

"Yep, that one" replied Fishlegs, who was moving swiftly around the board with his pieces, trying to claim the piece of my chief, but a solid defensive positioning from my men protected him.

"How and when did this happen?" I asked, as I moved some of pieces on to the offensive.

"Well, to be honest I'm not sure where I got the courage to make it happen. It was almost like a superior alter ego took over and stepped up to ask her." Fishlegs continued to take the attack to my defence but to no prevail. "I've seen her a couple of times in the pet shop when I was collecting food for Meatlug. And Mrs Jones had to go and make a phone call about delivery's or something, leaving me and her just there. And after a while we got talking about our pets and I asked her out for a date."

"Wow. So when is it, your date?" I asked. Fishlegs attacking strategy had left him in the open, I just needed a few more turns to gather enough support, before I could launch a full-scale attack on his Chief.

"Friday. And here's the thing she said to bring a friend." Said Fishlegs with a hopeful look in his eyes.

"Me? You want me to be your wingman?" I asked as I started to mount my attack.

"Yes, I do. I mean its not like your going to be doing anything on Friday are you?"

"I am." I said. "Don't you raise that eyebrow at me Ingerman, me and Toothless have plans of binge watching some tv program or something."

"C'mon Hiccup, I need your help. I can't exactly use Snotlout or Tuffnut could I? Snotlout, would just be Snotlout and Tuffnut would probably blow something up. Neither of them would help me impress Heather and you already know her, so it'll be fine." Replied Fishlegs, as he managed to take one of my pieces.

"Fair point." I am too well aware of the damage Snotlout or Tuffnut could do. "Ok so I'll be your third wheel then, lurking in the background getting bad pictures for your wedding in the future."

"Oh no, you won't be third wheeling. Heather is also bringing a friend."

"Please don't let that be Ruffnut" I begged.

"No, I think your like who it is."

"And who would that be then Fishlegs?" I asked as I began to sweep in on another victory.

"Astrid Hofferson." Stated Fishlegs. You, see Astrid Hofferson was my high-school crush and in fact despite not being at Berk University like the rest of the gang. She got a scholarship at 'Defenders of the Wing University to study Sport Science with Heather. "This is your chance to rekindle the one-sided romance you had" laughed Fishlegs.

"There was no romance between me and her, there were hardly any conversations between me and her. It was like she avoided me like a dragon would an eel." I said

"Nonsense, she was just going through a tough time, her Uncle had died in that house fire. They called him 'Fireman Fearless Finn' and she drifted away from everyone, not just you. Its part of the reason she went to 'Defenders of the Wing Uni' and not Berk Uni."

"Fishlegs, I really think this is a bad idea. You're win her over without me being there." I said, trying to suggest to Fishlegs another idea.

"The chance of me 'winning' her over increase by a tenth-fold if I have a wingman." Responded Fishlegs with a sly grin.

"Ok, fine I'll do it" I said as I swiftly moved my pieces into place to claim victory. "Good game, but you left yourself open to be flanked. Let me know the details for Friday ok?" I asked.

"Thank Thor, I didn't want to have to ask Snotlout or Tuffnut, that would be a disaster. And of course, though I don't know what were doing yet, but I'll let you know."

We then said are goodbyes and parted ways to go to our respective homes. It was all a bit mad to think in a few days he was basically going on a date with Astrid Hofferson after so long.

On the other side of town, Heather was having a similar conversation with Astrid.

"C'mon Astrid. It'll be good for you and the guy is quite cute as well." Said Heather.

"OK fine, its only one night and I guess if it means that you'll stop bugging me about it I'll do it, as long as its not Snotlout or Tuffnut." Replied Astrid

"No, it's not neither of them, but don't worry you'll be in good hands and company I know it."

"Who is it? C'mon you can tell me, I know you can. I know you want to" said Astrid as she tried to persuade her friend for a name.

"Nah, I'm not saying anything. It'll be a surprise" grinned Heather, knowing to well that Astrid was going to behead her with her axe when she finds out who it is.

So that's the wrap on chapter 1, let me know what you think of it in the reviews or any improvements that could be made to it.

As for the next chapter probably, sometime this forthcoming week.