A/N: There will be three parts-here's part 2

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Three Dates, Three Wingmen and one Ruffnut

Henry 'Hiccup' Haddock was astonished at how nervous his friend was. And how nervous he was as well. He had spent the day working on the assignment for his course at home, trying to ignore the empty cat bed, empty litter tray, empty bowls...and huge hole in his heart. He had neatly gathered up all Sharpshot's toys and boxed them but the little place felt empty without the lively ginger tom.

Felix 'Fishlegs' Ingerman had been his friend from Kindergarten and the shy, undergrown Hiccup had stuck to his friend all through junior school even though he had been ignored by the popular kids and bullied by some of the larger boys. He wasn't surprised that Astrid hadn't recalled him-when he left Berk High at twelve for Berk Academy, he had been a runt with limp light auburn hair, a mass of freckles and sarcasm that could melt steel-now he was definitely taller, more confident and his growth spurt had thickened and darkened his hair, sharpened his jaw and made him look very different to the boy he had been. Berk Academy had been his parents' idea and he had just about managed to maintain his friendship with Fishlegs, aided by Skype and their shared geekiness, though he hadn't exactly been fighting new friends off. His full scholarship to Archipelago University to study Aeronautical and Space Engineering had taken him away from Berk and he had finally found a girlfriend...but when his father started having chest pains, he had transferred back without hesitating.

Of course, Camilla hadn't wanted to leave the excitements of the main campus or the main island and so she had calmly and dispassionately ended it when he broke the news to her, any hopes she would transfer with him or at least want to remain with him brutally dashed. His father had been keen not to interfere with his duties or tip the press off regarding his illness so Hiccup hadn't moved home, though he had looked after his father through and after his angioplasty and stenting for what was blandly termed 'quadruple vessel coronary artery disease'. Mayor Stoick had no intention of taking things easy until his son had explained exactly what could have happened-and only then had he had agreed to take two weeks off and allow his best friend 'Gobber' Belcher to deputise for him. Even now, he was moderating his diary and taking more care of himself than he had for years...but his son refused to move home. Though bereft of cat and girlfriend, he was wondering if he was just being stubborn...until he recalled that Astrid Hofferson lived in his apartment block.

He honestly couldn't believe he had mustered up the nerve to ask out a girl he had harboured a crush for since he was about eight...and was even more astonished when she hadn't turned him down. And he would gladly have stood up Fishlegs if it meant he could spend he evening with her...but they had both honoured previous engagements so he would be spending the evening as Fishlegs's wingman, watching his friend drool over Ruffnut Thorston, who he was almost certain was two-timing his friend...and then he sighed. Maybe he could observe her and see if he could catch her out and protect his friend.

He checked his reflection: his tall, lean shape was flattered by the black tuxedo and pants, the polished patent black shoes, white dress shirt and emerald bow tie compelling the ensemble. He started as he heard Astrid arrive and race up the stairs and then he finished his preparations, brushed his wild hair into some semblance of neatness and went out when his cab arrived.

Fishlegs was waiting at the Great Hall and almost bouncing with anxiety. Tall, very heavyset with short legs, short blond hair and round greenish eyes on is pleasant, chubby face, he was a gentle soul and was genuinely delighted that Ruffnut was going out with him. He was clutching a large bunch of roses that probably cost three times what they would tomorrow morning and grabbed Hiccup's arm.

"Oh, thank Thor!" he whimpered. "The table's ready..." Forcing himself to smile, Hiccup led him in.

"Then let's get settled," he reminded his friend, eyes scanning the large space. very high and cathedral like, the Great Hall wasn't an easy place to make intimate, but they had used plants, balloons and the abundant columns to partition off the tables so each was almost completely intimate. There were candles on each table, crisp white clothes strewn with tiny red foil hearts and special Valentines' menus and the waiter led them to a four seater set up for a double date. Hiccup sat easily as Fishlegs changed position three times before ending up where he had originally started and then ordered Champagne.

"Um...Fish..are you sure?" Hiccup prompted him, seeing the price.

"Only the best for my Ruffykins," his friend said firmly. "A Magnum of Louis Roederer Cristal Rose 2007..." Hiccup peered at the wine list.

"Fishlegs?" he asked carefully. "Do you really want to spend over $600 on a bottle of champagne?"

His friend choked and waved wildly at the sommelier. "Wait!" The man turned with a small smile.

"I'm sorry, sir-I thought you wanted the best for your lady," he said, oozing superiority.

"Not at the cost of not eating for the next month," Hiccup took over firmly. The waiter tried to ignore him but Fishlegs was still choking at the thought of the cost so reluctantly, the smooth man turned back to the frowning auburn-haired man.

"Well, the cheaper option is the Krug Rose NV..." the waiter tried.

"At $700," Hiccup read. "Wow-cheaper means something different here. Usually it means 'costs less' not more." There was a frosty silence.

"Well, I can always recommend a Magnum of the Dom Perignon 2009 for the more discerning..."

"Wallet," Hiccup cut in. "Only $500. You're getting the hang of this. Wanna try again? Maybe with just two figures?"

Hiccup could have sworn the waiter growled at him and tried not to smile. "Well, for those of more parsimonious disposition, the Verve Cliquot NV Brut Magnum is..."

"Parsimonious?" Fishlegs squeaked. "You think I'm being mean?"

"About $130," Hiccup read. Fishlegs gulped.

"I've only got the for the whole meal!" he hissed.

"We'll start with a bottle of Moet rose, thanks..." The waiter gave an irritated sniff, snatched the wine lists and glided away. Fishlegs was already mopping his face with his napkin and almost fainting at the prices. Hiccup frowned.

"Why did you come here if you're tight on money?" he asked his friend and Fishlegs sighed.

"Ruff wanted it," he admitted. "And I am so lucky a girl like her is looking at a husky guy like me...I mean, she used to tease me that I was blocking out the sun sometimes-and now she's going out with me. I can't let her down...even if it means Ramen noodles for the next four weeks..." Hiccup eyed the menu and his eyes popped at the cost of oysters, steaks, raspberry champagne sundae to share and coffee

"Make that six weeks," he muttered.

The waiter returned, looked down his nose at the two men and poured four flutes of the pink fizz before stowing their bottle professionally in the wine bucket and walking away superiorly. Hiccup smiled as the sounds of steps pulled his attention back to the date. he sighed and automatically rose to his feet to greet their guests...

...and stared straight into Astrid's eyes...

oOo

Astrid froze as she stared into Hiccup's emerald gaze and she did a double take as she recognised the cute neighbour and cat-lover who was now definitely promoted to 'very hot'. Tall, lean, his silhouette flattered by the tuxedo, he was clearly as shocked as she was-and then he smiled, a genuine grin that made her heart flutter.

"I'm not sure they do pizza," he said gently. Fishlegs, who was fawning over Ruff, suddenly looked up.

"Oh, I'm sorry-I should introduce you, shouldn't I, snooky-poos?" he said eagerly, his big face lit with happiness. Ruff grinned.

"You got it, my big snuggly-wuggly," she teased him. Fishlegs squeaked in excitement and then looked at the others.

"Um...Astrid...this is Henry Haddock..." he began.

"Hiccup," Astrid interrupted and smiled at him.

"And this beautiful lady is Astrid Hofferson," Hiccup added, lifting her hand to his mouth and kissing it lightly. She blushed fiercely at the incredibly old-fashioned gesture. Ruff scowled...and then gave a gasp.

"The cute guy from the store!" she realised. "Hey Ast..." Blushing, Astrid grasped Hiccup's hand.

"Just right now, I wish we were doing pizza," she murmured and he nodded.

"Though currently, I'm more than happy here-since you are the most beautiful woman in the room," he told her sincerely, then quietly pulled out a white rose and handed it to her. "For you. I-I thought it was really presumptuous to give someone I've never met a red rose...so I thought maybe a white rose would be nice?" She carefully sniffed the rose and closed her eyes at the delicate scent: he had chosen a flower that was both beautiful and fragrant and she smiled, looking up into his hopeful emerald eyes.

"It's beautiful," she told him softly. "Thank you." He gave a smile that lit his face.

"Your smile is thanks enough," he said and then he groaned. "Thor, did I really say that?" She burst into giggles.

"Um...yeah..." she managed and he face-palmed.

"I'm sure they must pump some kind of hallucinogenic gas into the air," he suggested sarcastically. "To make sure everyone is acting completely crazy..."

"OOOH! Thanks so much! They're gorgeous, snooky-poos!" Ruff's voice was probably audible through half the hall as she flung herself against the husky young man extravagantly, though taking care not to crush the huge bouquet.

"I take your point," Astrid commented as they sat down, still smiling. They both sipped the champagne, savouring the dry flavour and studying the menu. She snorted. "Wow. Oysters-which are just ugly watery uncooked shellfish, which are supposed to be an aphrodisiac...then steak, presumably for strength...and then a fruit and alcohol pudding to share, all washed down with more alcohol...for how much?" Hiccup chuckled as Ruff and Fishlegs stared into each other's eyes.

"So basically, you are expected to leave here horny, drunk and poor," he translated and she giggled.

"Unless you're a wingman..." she reminded him. He inclined his head.

"I'm not sure you're not forbidden to have fun," he said thoughtfully. "As long as you do wingman duties..." Hiccup snatched a glance at Ruffnut and sighed.

"I know I have to right to ask you and I know you can't answer me but I have to check-because Fishlegs is my friend and he is a decent guy-is she cheating on him?" Astrid almost choked on her champagne and coughed a few more times before she looked up.

"What makes you think that?" she asked too quickly. His shoulders slumped slightly.

"Snotlout is my cousin and he's boasting about his new girlfriend..." he told her quietly. "Everything...including her name..." She stared into his face for a few moments...and then she nodded.

"I'm afraid so," she said softly. "In fact, it's worse than that because there's a third boyfriend in play and she's meeting all of them tonight in the Great Hall..."

"And trying to keep them all separate?" he guessed and she nodded. "And I guess you're here as a friend to help her...but I can tell you don't actually approve?" She nodded.

"Fish is a nice guy," he told her. "And he's really happy she's going out with him. I don't want to ruin the first Valentine's Day he's ever had a girlfriend for! But I don't want him hurt long-term either..."

"Me neither," Astrid confessed. "So you're gonna tell him?" His warm hand found hers and his thumb absently stroked the back of her knuckles as his bows dipped slightly.

"Not this evening," he told her after a moment. "I don't want him humiliated and hurt. So I guess I'm gonna have to help you keep her dates apart from each other..." Her eyes snapped wide. "And you definitely owe me a pizza date as well."

"Oh, Mr Skinny-you are definitely getting a date out of this...if we all survive..."

"I asked for the best table in the house!"

They both stiffened as Snotlout's voice wafted above the sounds of a string quartet wafting through the room. Astrid started and Hiccup groaned, seeing Ruffnut suddenly shoot a pleading glance at Astrid. She snatched a look into Hiccup eyes.

"Showtime," she whispered.

"I'll take care of him," he promised as Ruff rose, mumbling that she needed to go to the bathroom, hauling Astrid along with her. They spun to lean against a pillar behind a large umbrella plant and peered through at the confident shape of Snotlout, dressed in a bright blue tuxedo with a bright yellow bow tie, sipping a beer with another bottle placed waiting in front of Ruffnut's place. The girl in question stared and then leaned close to Astrid.

"Distract Fish while I spend a few minutes with Snotty," she ordered. "I'm in the bathroom if he asks. Tuff has promised to distract Snot when Eret arrives..."

"But aren't you sure you don't just want to spend the evening with Fish?" Astrid asked desperately. Ruff leaned close, her eyes uncomprehending.

"Are you seriously suggesting that I stand up Snotlout in favour of Fishlegs?" she asked incredulously and Astrid nodded.

"Look-he'll treat you far better than any of the others," she argued but Ruff was adamant.

"I'm having my dates and you, missy, can go back to making puppy eyes at Hiccup and his dreamy eyes," she sneered. "Cover for me..." And then she lunged forward, grinning broadly as she slipped into the seat opposite Snotlout, clanked her beer against his and smiled graciously as he presented her a small bunch of red roses. Astrid turned away as she accepted the sloppy kiss he gave her and then she slid back into her place opposite Hiccup, seeing Fishlegs's eyes drift worriedly towards the restrooms.

"She's going to be a few minutes more," she said, hating herself for lying. "I think she may have a slightly upset tummy. It must be the excitement of the date-which she's been talking about all day." That much was true. "And she's very highly strung..." Shoulders slumping slightly, the husky guy sipped his champagne and nodded.

"As long as she hasn't run away and bailed on me, I can wait," he said and Astrid stared into Hiccup's equally uncomfortable eyes. They were both silently saying the same thing:

She doesn't deserve him.

A movement in the corner of her eye drew her attention to a tall, buff shape walking confidently to the table almost next to them-and she gasped as she saw Eret Eretson sit down in almost full view of Fishlegs.

Eret who was Ruffnut's third date.

Frantically, the blonde made surreptitious gestures to Hiccup, whose eyes widened in recognition and then understanding.

"Seriously?" he mouthed and she nodded. "Well, she really doesn't have a type...except possibly 'male'..." he muttered. "Should I be worried?" Her eyes widened and she gave a small nod.

"Well, if you want to be, you can," she hissed. "But I'll protect you from the man-eating lunatic blonde..." He quirked his lopsided smile.

"And we're not talking about Tuff," he smirked then signalled a waiter, pulling the man close and whispering a few words in his ear. He handed over a fifty dollar bill and the waiter smoothly pocketed it, then walked professionally over to Eret.

"Excuse me, sir-I have been made aware that there is a particularly cold draught blowing over this table and I would like to offer you a superior alternative..." He gestured to the table just behind Hiccup, a large plant shielding Fishlegs-and Ruffnut, when she returned-from view. As expected, Eret rose and graciously accepted the 'superior alternative', sitting down and ordering a whiskey. Unthinkingly, Astrid's gaze slid over the man, his buff and tall shape flattered by the white tuxedo with a white dress shirt and black bow tie. His long raven hair was pulled off his face in a thick ponytail and his large chin was decorated with traditional Inuit tattoos as a nod to his heritage. His caramel eyes flicked up, noting her inspection and she lowered her eyes, blushing. Then, as she glanced up again, he gave a cheesy grin, tipped his glass to her and winked.

Her eyes widened and Hiccup noted, his brows dipping.

"Are you okay?" he whispered and she paused.

"Eret is winking at me," she said neutrally. He stiffened.

"Um...really?" he asked, a note of uncertainty entering his voice. Her eyes snapped back to his face and she grasped his hand. As if she would trade a guy who winked at a woman clearly here with another man in favour of Hiccup! Hiccup who she already felt as if she had known forever...

"You have nothing to worry about," she said intensely. "I was just shocked. I mean, he's here to meet with Ruff but he's just winked at me and then nodded and tapped his watch. He's asking me to meet up later. Ugh! The slime..." Hiccup pressed his lips together, momentarily looking annoyed and then his eyes crinkled in a smile.

"I think we can do something about that," he smiled and signalled the waiter again. "I have an idea..."

Suddenly Tuff-dressed as a waiter-appeared from behind a large rubber plant.

"Argh!" Hiccup gasped, pressing his hand against his heart in shock. The male twin grinned.

"Nothing to worry about, my man," he said cheerfully and then did a double take. "Hiccup?" The auburn-haired man frowned.

"Tuffnut Thorsten? Oh my Thor...what are you doing here?" he asked. Tuff grinned.

"Assistant wingman to my sister," he hissed, still lurking out of view of Fishlegs. "Of course, Astrid here is numero uno sidekick..." Astrid growled.

"I am not a sidekick," she snapped. "I'm actually enjoying my almost double-date...if your sister would reappear and none of the rest of your shenanigans were going to happen." Tuff burst out laughing.

"We're Thorstons!" he reminded her. "We worship Loki-so chaos and disaster follows in our wake!"

"Wait-you know Tuff?" Astrid asked, eyes widening. Offering a small smile, Hiccup gave a single nod.

"I know you all," he told her gently. "We used to go to school together. We even played together in preschool-but when we started Elementary School, you became friends with all the popular kids and I..." He paused and there was an uncomfortable silence. "Well, you and most of the other kids ignored me. I mean I was kind of small and skinny and frankly a mass of freckles so no one paid me much attention. I git sick a lot as well...and when Mom died at the start of Middle School, Dad moved me to Berk Academy..."

She blinked and even more guilt crashed over her. She had completely forgotten about Hiccup...but the handsome man with the syncing emerald eyes facing her was so different to the skinny kid he had been and she had just forgotten him, what with High School, college, relationship troubles...

Then his warm hand closed reassuringly on hers.

"But you were never mean to me, unlike some people-and we all make mistakes," he told her kindly. "Honestly, if we had been in High School together, would we be sitting here today? I'm a very different person today than I was back then and I'm sure you are too. So maybe we should just pretend we're just a boy and a girl, out on Valentine's Night and try to enjoy this date?" He smiled at her and her heart fluttered. "I believe everything happens for a reason, Astrid-so maybe we should see what happens..."

"You mean apart from helping your date's insane best friend try to go out with three guys simultaneously..." Astrid said and sipped her champagne. The waiter delivered shucked oysters with chilli, lemon and ginger and crisp white wine as Astrid stared at them dubiously. Hiccup snorted with laughter.

"You don't look convinced," he noted in amusement.

"They're raw!" she protested. "And they're slimy and bleurgh!" Meeting her disgusted blue eyes with a twinkle, he chuckled and ate the first one, swallowing quickly.

"They'e actually really fresh and tasty...but if you don't like the idea..." he murmured and winked to the hovering waiter, who swapped the oysters out for grilled Tiger prawns that he had ordered earlier. Her eyes widened and she gave a brilliant grin.

"Thank you!" she said happily. "How...?" He ate his second oyster.

"I guessed when we discussed the menu," he told her smugly. "I mean, oysters aren't to everyone's taste...and though the whole menu is supposed to be aphrodisiac, the fact that people go out and drink tons and expect romance is probably a better explanation why there is a spike in births in late October/early November..." She stared at him in shock.

"Are you serious?" she asked him, sucking the sauce off her fingers from her prawns. He nodded, eyes twinkling. "How did you know that?" He blushed.

"Um...it was a project I did at school," he admitted, suddenly self-conscious. "I was asked to relate the changing patterns of birth rates to calendar events and..." She smiled at his sudden discomposure.

"So you were basically having to work out why people suddenly had loads more unprotected sex?" she teased him and he suddenly went beet red. He nodded and she smiled at him, patting his hand. "Good work," she said more assuredly.

"Hey!" Tuff elbowed him and he sighed in relief. "Distract Fishman-I'll get sis for her appetiser..." The male twin vanished as Eret checked his watch and winked at Astrid again. Reading her face, Hiccup sighed, then leaned towards Fishlegs and murmured a few words to his friend. Hiccup was kind and made sure they talked, sharing geeky facts about extinct dragons, which they clearly both loved....

Peering through a gap in the plants, she could see Snotlout swigging his fourth beer with Ruff leaning across from him, almost finishing her third and necking her oysters at top speed. As if on cue, Tuff appeared, tapped her shoulder and whispered in her ear. Then she grinned.

"Sorry, babe," she said, pouting. "Tuff needs me for something. You have another beer and I'll be back soon..." She kissed his nose and he grinned cheesily.

"Hurry back, babe!" he said and snapped his fingers to get the waiter to bring him another beer. Tuff rolled his eyes as Ruff straightened up her dress, took a deep breath and swept back to sit by Fishlegs. She took his hand and smiled happily.

"Sorry, snuggly-wuggly," she said in an apologetic tone. "I was a little queasy and just needed a little fresh air to settle myself down and I'll soon be...oooh! Oysters!" And she launched in to start scarfing them down at a rapid pace. Eyes popping, Fishlegs smiled and joined her, chatting in a concerned voice that completely had Astrid feeling ashamed she was helping her friend in this deception as she and Hiccup watched.

"Is she really going to eat three whole meals?" he checked and she nodded seriously, finishing her last prawn.

"Of course she is," she told him. "It's free and there is nothing Ruff won't do for a free meal..."

"Even going out with three men all at once?" he checked.

"You're lucky," she reminded him. "If I hadn't spoken to you, she would have jumped you in the Pet Depot!"

"Oh, thank Thor that didn't happen," he said in relief. "But is she really going on with this?" Astrid nodded as Ruff clutched her middle, kissed Fishlegs and staggered away...until she had rounded the plant and then straightened up, grinned broadly at Eret and slid into the chair opposite him.

"Hiya, handsome," she grinned and leaned over to kiss him. "Sorry-I was held up..." He grinned.

"I almost gave up," he said, his eyes wandering to inspect Astrid over Ruff's shoulder. "I got you a mead and sour-just how you like it..." She kissed him again and grabbed the drink, then sat and swigged the amber liquid before stared down at her third plate of oysters. She grinned and tucked in, laughing and joking with her date.

Fishlegs was getting more and more down and not even Hiccup could cheer him up.

"I thought this meal would be a chance to spend time with her," he said despondently. "I mean, she's incredibly fun and wild but I just wonder whether she is the one for me? Every time I try to get her to do something I really enjoy, she yells 'boring' and insists we go down the Tavern. Or if we go out, it always has to be something insane and dangerous." He stared at the table. "I mean, I like birdwatching..." Astrid sighed.

"Fish-you're a really nice guy and I know Ruff likes you," she began as she felt the weight of Hiccup's eyes on her, wondering if she would try to make excuses for her friend. She swallowed. "But you are so different to each other that I'm not sure if this is long term?" She toyed with her napkin. "I mean, being grateful someone is going out with you isn't the best basis for a relationship. There does need to be give and take. And you have to decide whether you are happy with her." He stared at her.

"You think I'm not happy?" he asked her in surprise. She nodded.

"I think you undervalue yourself and are willing to accept...less," she told him kindly. "And you should never accept less." Hiccup stared at her in shock and realised she was talking about herself as well. She smiled, her cheeks flushed as she felt his eyes on her. "And yes, I learned the hard way. So don't make my mistake, Fish-don't sacrifice what you want and your own happiness of someone else who may or may not be faithful..."

He stared at her in shock and drained his glass. And then he waved to the waiter.

"Bring me another bottle," he said.

A table over, Tuff was consoling a very drunken Snotlout, who was wondering if Ruff actually loved him. "I mean-aren't I a nice guy? Aren't I handsome enough?" Tuff sat opposite him and patted his arm helpfully.

"You're a great guy, one of my best friends and the best mate a Thorston could want," he assured his friend, leaning forward and idly finishing his twin's half-drunk drink. "And I know that Ruff loves spending time with you..."

"Then why isn't she here?" he asked, sniffing. "She said she was with you but you're here..."

"...and she's with Astrid," the male twin continued seamlessly. "Look-Ast is her best friend and she's boyfriendless and sad and sometimes, she has to be a friend as well as a girlfriend...you understand, right?" Snotlout sniffed, wiping his eye.

"I guess," he said, sitting back and swigging his beer. "I've always liked her...well since Astrid threatened to bury me alive if I didn't stop bothering her...and then when Ruff said she would come out with me, I knew finally things were going my way." He paused and stared at his beer. "I mean, I know I'm dumb...but I work hard at Dad's scrap business and I am trying to be more responsible...so why isn't she here?"

Tuff sagged.

"You got a Thorston right here," he reassured his friend. "And I'm with you, no matter what my insane sister does-you know that?" Snotlout sniffed and nodded.

"I know," he sighed. "Another beer?" Tuff sighed and nodded.

"I know I need one," he admitted.