My first new story in forever. I was inspired by re-watching a playthrough of Sonic Chronicles and the whole Dexter subplot. The only definitive thing we know about the guy is that he's a pilot and owns a plane, so I just filled in the blanks. While I do ship Sonamy a lot, my headcanon is that when Amy gets older, she would be receptive the idea of dating other guys but her heart would still linger for Sonic, so I finally wrote a fic about it!

Disclaimer: I don't own the Sonic Franchise.

Ages:

Sonic: 24

Tails: 17

Amy: 21

Dexter: 19

Cream:15

It had been months since Sonic had been in Station Square. When you are the world's fastest hedgehog you could travel anywhere in the world, but Sonic would always find himself back here. Sonic finished his nightly run and decided to take it easy, uncharacteristically taking a walk around the block.

'When ya' go slow, the city's completely different.' Sonic took time to listen to the noise of late night traffic and owls howling in the distance. Urban life never did stop and Station Square was a city that never slept. Sonic observed noticed lots of people still out and about; Late night shoppers, businessmen, partiers. Sonic gasped. Being lost in his thoughts almost got him in the face by the burger shop door.

"Hey! Watch it!" He called out irritably at the perpetrator, but his cries were lost on deaf ears by the human couple who walked out of the restaurant.

"Oh, Tom this was the best date ever!" The girl was gripping the man's arm in happiness Sonic guessed. "It's nothing really, Maddie, anything for you." The man replied as she gave him a small peck on his cheek. Sonic automatically pretended to throw up. While he was years older, Sonic had never opened himself up romantically. He was still emotionally a boy in that regard. Although seeing that couple together did make him wonder. 'I haven't seen Amy act like that in years'. In a warped way, it made him feel nostalgic. By chance, he realised he was strolling past the entrance of Twinkle Park, still boasting its promotion of 'Cute couples get in free!'. Sonic had lost count of all the times Amy tried to make him take her to the theme park. Sonic looked out towards the coastline, watching how the moon reflected in the sea.

'It's getting late. I should head back to Tails' place.' Sonic sped off, proceeding to jump from rooftop to rooftop to have some fun before the last train to the Mystic Ruins arrived. He stopped to rest one rooftop to enjoy the skyline over the city.

"Ugh, another horrible date." Sonic's view was interrupted by a familiar voice below on the top floor balcony. 'Amy?...'

"I don't think I can take any more of this." Sonic peered down to see a pink hedgehog in a nightdress, talking aloud on the phone as if she were talking to the entire apartment block. Sonic leaned in curiously, it wouldn't count as eavesdropping when she was broadcasting her private business to the whole city.

'Yep definitely Amy.'

"No more blind dates, Cream."

'Dates?! She's been going on dates?!' Sonic was shocked. Amy never gave any indication that she was seeing other people. Part of him was happy that Amy seemingly has moved on from her childhood infatuation with him, but another was confused. On the rare chance, Sonic met up with her, her love for him did not seem to dissipate, only expressed more subtly. He made no sudden movements to make sure he was not caught. Amy catching him now would lead to more questions than answers.

"I'm sorry, Amy. I really thought it might work out this time. I'm sure he was nice." Cream's passive voice was muffled by the poor signal.

"That's not the point! He wasn't my type at all!"

"What is your type anymore?"

"He has to be romantic, courageous, kind, dashing, fast and-"

"So Sonic?" She interrupted innocently but nonetheless made Amy whine at being caught out. "You are so picky, Amy. I just don't want you to be lonely without Sonic around. Please go on one more."

'Amy's... lonely.'

"It's okay, Cream. Please don't worry about me anymore. I'm happy being single, honest. We'll talk later." Amy hung up the phone and groaned out to the world. "If only Sonic were here." Amy then left the balcony sniffling, releasing small tears from her eyes. Sonic wanted to jump down into her apartment and cheer Amy up, but emotional topics like this were out of his element, especially on the topic of love. Amy would inevitably talk about their own relationship or lack thereof. How many dates had she been on? How long has she felt this way? Sonic remembered that when you run faster than the speed of sound, everything, even the little things, pass you by.

The Next Day

On a summer's day high in the sky, Sonic and Tails were taking a test flight in Tails' newly built Tornado 3. While Dr Eggman had taken a significant break from attempting to take over the world, Tails thought it was the right time to design a new plan of his design that would surpass his own Tornado 2 and Sonic's original. Tails was focused in the driver's seat, muttering to himself about the plane's current altitude and coordinates. Meanwhile Sonic amused himself in the passenger's seat, observing the lush views of Emerald Hill below, taking in the dual warmth and cool breeze air transportation provided.

It had been years since the duo had gone on a flight so peacefully. With Dr Eggman seemingly out of the picture, Sonic enjoyed the days of tranquillity the villain's absence afforded. Tails could freely work on engineering new technology that could aid mankind rather than weapons. Tails' technobabble was still lost on Sonic, but his words have sunk in as he helped develop the Tornado 3 based on his limited knowledge of the first model. Knuckles got his wish to stay on Angel Island full-time guarding the Master Emerald with only Rouge serving as his only distraction.

While Amy... could finally live the life she wanted. She was now a working woman, living a semi-modest life in the city. No longer the little girl he met on Little planet all those years ago. Her age and experience made her more mature physically, but at heart, she was the same. Until last night, it'd had been a long time since Sonic had seen Amy. She was always busy working at her bakery whilst he was still on the run. They never ran into each other anymore outside holidays like Christmas and it didn't help that Amy never actively sought him out anymore. The Mystic Ruins were long ways to travel just to see Tails, let alone Sonic.

'Bet she can she can still run like a linebacker,' he joked until Tails interrupted his thoughts.

"It looks like the Tornado 3 is running smoothly."

"Much better than the last couple of flights." Sonic quipped, "You really outdid yourself this time, buddy!" He yelled over the engine.

"Thanks, Sonic. We can head back to the workshop, now that I have more data to work with."

Sonic's belly rumbled. "Great, 'cause I'm starving." Tails laughed. It felt nostalgic to fly with Sonic again. Sonic may have aged, but his attitude certainly did not.

"At least this test flight didn't end with a crash," Sonic said jokingly, causing Tails to face Sonic with faux anger. "You'll never let forget-"

"AHHH! MAYDAY! MAYDAY!" Distant screams filled the air. The clouds blinded their vision as they tried to find the source of the SOS. The clouds cleared to see a small biplane heading straight for them, causing the hedgehog and fox to scream until the opposite plane took a sharp dip toward the ground.

"Who was that?" Tails asked confused and still recovering from their almost crash.

"Doesn't matter! We gotta' shift into gear!"

"Roger!"

Time looped once again. It was like old times. The start of another adventure. Sonic and Tails dove down to land in Emerald Hill, trying to avoid hitting the trees near the wreckage of the tiny biplane. They were greeted by a large gathering of Flickies flocking around the body that limped outside the vehicle.

Sonic helped the victim stand straight whilst Tails calmed down the animals and made them disperse. "Hey, dude, are you alright?"

The victim coughed, getting the gas fumes out of his system. "Yeah, I'm fine." The man pushed away Sonic's arm and stood himself up. "Sorry, for almost crashing into you guys, I didn't think anyone would even be around to help, but I guess I was the lucky one in the end, hehe." His was voice low and had a slight drawl. He did not sound like anyone he knew, but he seemed familiar. The man, or rather, hedgehog, wore a burgundy flight suit which contrasted his tan yellow fur. His clothes and black boots were all dirty and scuffed from the crash, and his quills were covered with soot.

"Well, we're glad you're okay, Mister..."

"Dexter," The burned hedgehog extended out his hand to the fox. "Nice to meet ya'"

Sonic retreated into his thoughts, 'That name sounds awfully familiar.'

"What were you doing flying all the way out here Dexter?"

Dexter laughed. "I should be asking you guys the same thing. To think the famous duo Sonic and Tails would be flying in my neck of the woods. My friends back home won't believe it."

"Sonic and I were in the middle of a test flight when we, or rather, you ran into us."

"Small world. I was just doing the same when my engine malfunctioned." Dexter looked over the wreckage and sighed. "It was her first flight, but now it'll probably be her last." Tails surveyed the damage. It was a primitive build of an aircraft, barely on par with Sonic's original Tornado. Tails was impressed it could even fly at all.

"Did you build her all by yourself?" Tails asked inquisitively.

"Nah, my Pops did, although he could never get her to fly. I've only just learned to fix machines and pilot 'em but I'm not a genius like you are Tails. I could never fix her. She's too old."

Sonic ran his hand by the side of the wrecked plane. The wings were hanging on for dear life, the propeller somewhere in the ocean and the once clean paint job was now a shell of its former self. "I wonder... Why don't we fix up?" Sonic offered.

"Really?!" Dexter could not help but look starry-eyed at the heroes.

"The Tornado 3, is practically finished now, and Tails could use a new project. What do ya' think, Tails?"

Tails remained silent, still observing the wreckage. He suddenly turned around to the hedgehogs and smiled. "I'll do it! It's been a long time since I've worked on a small plane like this. I'll get the Tornado and we can tow it back to my workshop."

Dexter excitedly shook Tails' hand in awe. "Wow, how could I ever repay you."

"Don't worry about money. We'll figure out payment later. Just consider yourself on a tab." Sonic quipped while winking.

"I've never seen a plane so advanced. Even the cargo planes I work with can barely hold a candle to the nado'-3" Dexter noted, admiring Tails' machine. The two mechanics were drawing blueprints and contemplating where to start rebuilding. "Dexter, could you get my welding tool, it should be somewhere in the storage room."

"Sure, be right back." Dexter disappeared in the back room. Sonic meanwhile was relaxing on the couch in the main room outside in Tails' house which was connected to the workshop. Sonic may have learnt a lot from Tails about mechanics but that does not mean he absorbed the theory. Sonic and Tails both agreed he was better for the heavy lifting. A knock on the door interrupted his relaxation. "It's open," Sonic lazily called out to the visitor.

"Sonic?" The door opened to reveal Amy Rose holding a wicker basket. Sonic almost fell off the couch. He had not seen her (in person) in months. She was smiling ear to ear, if Sonic did not know Amy cried herself to sleep last night, he would have been fooled. Amy was dressed comfortably in her favourite red dress and boots, although since she matured, she and Vanilla altered it to be longer and fit her new size. To Sonic, Amy looked practically the same only with slightly longer hair, but he was never one to notice the small details. Regardless, the new independent aura she had let him know she was growing up gracefully.

"Amy." Sonic got up from the couch to greet her. "What's the occasion."

"Oh Sonic, I didn't know you'd be here." She was visibly flustered; it was a surprise to catch Sonic anymore. Every time she asked about his whereabouts, it was always different; Spagonia, Empire City, Adabat. They were never on the same continent at the same time these days. Even when he was in Station Square, without fail she was on vacation or a business trip. 'So unfair,' Amy lamented.

"I came over to give Tails some goodies. Every week there are leftovers, so I give them out instead of letting them go to waste."

Sonic looked into the basket to find a sweet array of baked goods; cookies, muffins, anything a sweet tooth would love. He dug his hand down Amy's basket quickly before she shooed his hand away. "Those are for Tails' to pick first."

Luckily for Sonic, he picked out a raisin filled cookie and started eating it loudly. "Hmmm," he moaned in delight. Amy's cooking was always great, he missed eating her treats.

"You got any chocolate chip," He inquired, still aggressively chewing on the sweet treat.

Amy gasped, 'Why didn't I pack them just in case!' She was upset by her lapse in judgement but more so by Sonic's never-changing sloppy eating habits. "Not for hedgehogs who talk with their mouth full." She replied with her nose in the air and made her way to Tails' back room where the workshop was.

Sonic chuckled as he finished the cookie. 'She's so fun to tease.'

Amy was walked into a workshop in disarray. Tails was writing notes on his desk. "Tails are you busy."

"Nope," Tails immediately noticed the fresh scent of baked goods. "Is that mint I smell?"

"Yep, it's all yours, but since Sonic's here now I guess you'll have to share."

Sonic entered after Amy, content with his snack, but not selfless enough to stop himself from taking more from the basket. "Tails, how long have you been holding out on me?"

"By the time you visit, they're all gone." Tails retorted as he sucked on a mint lollipop. "If you visited Amy more often, you'd be getting all the leftovers." Sonic stuck his tongue out at Tails yet agreed that if he stuck around more, he would not be losing out.

"Well... if you want. Instead of leftovers, you can try some of my free samples, if you come by the bakery today. That is if you're not busy working with Tails." Amy rubbed her palms. It was rare for Sonic to see Amy so coy. "Erm, sure, why not." Sonic smiled, trying to tease her nervousness, it was the least he could do after last night. Amy smiled in return and suddenly hugged him with all her might, making Sonic's third muffin almost fall out of his hand. No matter how domesticated, Amy Rose was still a tough cookie, but it was nice to see her bubbly self.

"I'm experimenting with new flavours. If you think these tasted good, your taste buds will be in for a shock!"

"Ack! Amy, can't breathe."

"Sorry." She apologized and let him go, released a girlish giggle. "It's only because it's been so long. The bakery's always packed and I'm always so busy cooking, and you're always away. Maybe afterwards, we could go to a cafe to catch up... " A beep from Amy's watch stopped her train of thought. "Oh, I better get back. The bakery always gets busy after lunch." Amy quickly rushed out of the workshop but left her message in her stead. "Don't be late Sonic, I'll be waiting." Amy's voice seemed to echo throughout the workshop until the door slammed behind her. Amy's words last night haunted him. Sonic knew he should go but worried about their innocent hang out turning into something more unsavoury.

Abruptly, Dexter slid back in the room as if in a trance. Tails noticed this and apologized. "Oh, Dexter you're back. You just missed Amy, but she left some treats."

"No, it's alright." Dexter dragged himself over to his plane and laid against it. "You okay, Dexter?" Sonic asked.

"You're so lucky, Sonic," He placed the welding tool on the des next to Tails, took a muffin and sighed. "To be able to see such a beautiful girl like that every day."

"Who? Amy?" Sonic and Tails replied simultaneously. "Yeah." He took a bite of the muffin and grinned. "Even her cooking is sweet. I was lucky enough to be metres away and I still missed her."

Gears started to spin in Sonic's mind. A dangerous smirk appeared on his face. He sped over to Dexter and put his arm around him. "Sooo you're a big fan of Amy's right." Dexter blushed. "As big as everyone else is."

"Oh, come on, Dex, we're all guys here." Tails could not help but notice Sonic's sudden overfamiliarity with their new friend. Sonic was never 'touchy-feely' with anyone, let alone someone he just met. 'That smirk means he's up to something.'

Dexter let out a nervous laugh, "Well, she is very pretty. I've always admired her. I would be lying if I didn't wish I could go out with her as a teen."

"Well why don't you?"

"Wh-What?! I could never... A city girl like her would never want to date a country boy like me," he sighed. "Besides, it would be rude, since well, I thought you two were an item?"

"Me and Amy!?" Sonic removed himself from Dexter and shook his head. "No way!"

"Oh, I guess that was rumour after all. People have spreading that one for years. Cool to hear the truth from the horse's mouth though." Sonic winced. He never cared about what publications thought about him, especially those gossip magazines, but it was still embarrassing to have Amy's declarations of love from years ago be considered gospel without his contradicting statement on the matter.

"Forget that. What if I told you, I could get you a date with her?"

"For real!"

"That is... if can you be ready for 3 o'clock." Dexter stared at the clock and panicked. "That's 2 hours from now." His overalls were still covered with dirt and oil from the crash. "I need to get ready. Do you mind if I use your bathroom." Tails nodded and Dexter scurried off into Tails' house to freshen up.

"Sonic... What are you up to?"

"Who me?" Sonic responded sarcastically with a wry smile. "I'm just helping a guy out. You worry too much."

"Are you going to tell Amy?"

"She doesn't need to know. It's a surprise. And before you say anything, I'm still going to meet her in town later. Dexter will just take over romantic second half. He's a nice guy."

"Sonic, you don't even know him!"

"Tails, have you talked to Amy recently?" Tails shrugged. "She needs love. All I'm doing is making a friend happy. No ulterior motive."

Tails went silent. He too had hadn't kept contact with Amy a lot since they were both busy in their respective fields. The few times they did speak, it was either about Sonic, her relationship issues and why her relationship issues were somehow all Sonic's fault. It had been years and she never seemed to move on from wanting Sonic, even if she wasn't gushing over him at every opportunity anymore. Amy would be happier with some sort of love in her life if Sonic was never going to reciprocate her feelings. If Amy and Dexter got together that could kill two birds with one stone.

"Okay, Sonic, I believe you, but I have a bad feeling about this."

"Come on Tails. For all we know they could get married tomorrow and then you'll be the fool."

Tails sighed. 'This cannot end well.'

I hope you all like the first chapter. I think it's my longest. I've read very few stories where Sonic's the one playing matchmaker so this will be fun to write. I imagined what Dexter looked like based on my own interpretation. I can't draw, so hopefully my descriptions help. Next chapter be primarily from Amy's perspective so we'll get an insight on how she perceives her love life. For someone like Amy who is every emotional and has strong feelings and attachments towards her friends and Sonic, I imagine not seeing them often would affect her more than the others.

Thank you for reading and please review to tell me how what you think.

See you all next chapter!