A/N: Next Gen AU, Portrait Tom Riddle/ Portrait Cedric Diggory, with Teddy Lupin accidentally being a matchmaker.

"I find the best way to love someone is not to change them, but instead, to help them reveal the greatest version of himself."— Steve Maraboli


Strangely, it had been Teddy that had started the communication. He had been a young boy, small but still filled with big dreams. Before he had been eleven and a student, Teddy had been given permission to wander Hogwarts when he and his godfather, Harry walked in the hallways and while they've talked with some of the professors. In those occasions, Teddy had watched and chatted with the portraits that had welcomed him. He loved it.

They all each had their own stories, with all the different colors and palettes awing him when he visited each time. They all had their landscapes and moods. It made the wizarding world always fascinating for him.

For Teddy, it had been fun to interact with them. The conversations almost perfectly mimicked real people. And that had been why he wanted to talk to them. Tom and Cedric. They were both two interesting people.

One with dark hair and fair skin that hardly conversed with others. He somehow always had to sport a borderline sneer close to his lips when anyone tried to actively talk to him. (It somehow reminded him when his cousin Draco and godfather were in the middle of a passionate argument. Like for quidditch games or when Uncle Harry wore the jumpers that made cousin Draco feel disgusted to be seen next to him.) He could be friendly enough, and for Teddy, he liked Tom well enough.

He just needed help in having friendly conversations.

Which, reminded him of Cedric. He, who was bright and cheerful at first glance, he had that type of aura around him. Cedric had been a great person when he had been alive too apparently. Although, Teddy would never get a straight answer from anyone that had known him no matter how many times he politely asked or overheard, he just knew the bare minimal that he knew that Cedric was the perfect first portrait friend for Tom to have. They were two opposite personalities that Teddy wanted to interact. And Cedric had humored him too in that day when he asked him if he would help Tom loosen his walls and shields, he kept since his portrait had been discovered and allowed to be put inside Hogwarts.

The older Hufflepuff had liked the idea more when he had finished asking him. And, it had kicked it off when Teddy spirited through the summer hallways. Hogwarts had been a little quiet but, it still had made Cedric smile as he followed Teddy. His godfather Harry, in the background had looked confused but allowed Teddy to wander around. Nine years old was old enough to have some freedom, especially when there were house elves and other thousands of portraits to watch over him.

When he first saw him, Teddy had remembered how pretty the background had been. A sleek couch, a wide library with sunlight that only spring could have had made the room cozy and refined. Tom had been painted wearing a nice relaxed white shirt with ironed slacks and polished shoes. His hair had been sleek too, and when he looked at Teddy his face had been pretty. (Even if it morphed into a scowl and hesitant nod when Teddy lingered in front of him.) He had been able to see how lonely he had been too, as other portraits watched Teddy smile at Tom.

At that time, Teddy had given his name, but he had not known Tom's name. No. It hadn't been simple back then, Teddy had tried his best but it had been Uncle Harry that answered it when he called him out. He had been about to call him out again, but when he noticed who he was introducing himself to Uncle Harry had automatically reached over to firmly pull Teddy away.

"Tom?" His godfather's voice had been deadly calm. He had questions, of course, and as tense as he had been back then, Teddy knew his godfather would find whatever answers he wanted soon enough. "I never figured you'd be the type to have portraits of yourself back then. Not until—" He stopped himself when felt Teddy's glaze.

"Never mind that, how are you?"

He still looked both output for having to run into someone he knew before. The same kind of look reserved for when Teddy knew that meant Tom had been something related to his godfather's past. Either for the war he fought or school related.

Tom, who had been carefully analyzing them didn't look surprised of how protective his godfather had been.

"I am fine. However, I do not know you." His body still had resembled like a caged animal. "I was created during the very beginning of my fifth year in Hogwarts back in 1942."

It had been a big deal. For Uncle Harry at least, but he never did find out when Teddy had still been a young boy. Yet, Teddy understood that Tom, and Uncle Harry had a history with each other, just not the portrait that they both found in Hogwarts. But it still had been the beginning when Teddy knew what he wanted to do with Tom and his lonely corner where his portrait had been displayed.

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One well-known fact about Teddy Lupin, is that once he wanted to be friends with someone, he would do his damn best to achieve that. Whether they were animals, portraits, or people, Teddy had known his role in the world. His own heart had been shaped for that kind of love and empathy. It had been why it had been easy to persuade a kindred spirit like Cedric to join his cause. They both, Teddy and Cedric were willing to be friends with him.

There were no hidden agendas.

Even if at first Tom had been hesitated and very standoffish when Teddy had announced his and Cedric's arrival. With Cedric being a portrait person, it had given Tom more subtle reactions as Teddy coaxed Tom to allow Cedric to get closer. That day Cedric didn't step inside Tom's domain, but he had been able to introduce himself.

It had been a taxing and slow afternoon that day, but Teddy had been happy that Tom did not outright banish them. Or the next day or the day after that. But he had been jealous that Cedric had more time and opportunities to greet Tom than Teddy could. The nine-year-old didn't deny it, but he had also been very happy to hear that Tom had slowly been nodding off to Cedric's babbles. (It still had been a little rude that Tom read his books when Teddy and Cedric talked to him, but Teddy had also been stubborn and practically punctual with his greetings.)

Those first days had turned to weeks. Before he knew it, Teddy had to say goodbye. It had been sad that there had not been a portrait he could take for Tom and Cedric to visit him back at home, but with Hogwarts starting again Teddy had managed to have some hours dedicated to Hogwarts during the holidays, provided that a professor or other adult with permission to be in campus would be there to monitor him.

But that had been good enough for him as he noticed Tom getting used to their company.

Just as much as Teddy loved seeing Cedric's youthful face smiling bigger each time Teddy waved at him. Or when he found out who his parents were.

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"Your mom was Tonks? She was a brilliant Hufflepuff."

Cedric had been a little shocked when he saw Teddy's hair spontaneously switch colors. But he had also been quick to smile and reassure him too. He could see why Cedric had been made a prefect.

"And also, Professor Lupin too? Incredible. He was of the best Defense teachers I ever had the pleasure of having. You have both their best qualities. (They would be proud of you, and the person you are becoming.)"

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With his smile and kind eyes seeing him, and taking in his features Teddy had always felt comfortable when he visited Cedric. He was like the perfect big brother and sort of uncle that a portrait could be. And companion when he checked on Tom. The winter season had been kind, with the layers he wore and not the multiple ones that he would need later on as December roared. Since summer, Tom had still been stony in some topics.

But it hadn't been that bad. Unlike his godfather, his cousins Draco and Ginny had accepted his bundling friendship with Tom. They had also memories with other versions of Tom. One with an old dairy, and one of an older man. They never told him the whole stories, but they had also seemed to understand what Teddy wanted. As well, they had in turn visited Tom in Hogwarts during the Winter Holidays.

It had been awkward.

When it concerned cousin Draco, Teddy had caught his skin turn pale and somewhat stiff when Tom looked at them both. Cedric had not been there, but Teddy's warm smiles had done a decent job for Tom to get a feel of his future (and very dead) version's outcome. His mood had been sullen and reluctant, but Teddy had also been careful when his cousin Ginny's turn had been a little more talkative. In her end, at least with her red hair pulled into a tight bun and Luna by her side.

Tom had answered their questions, but they all knew his replies would never mean much. She had known Dairy Tom, and Portrait Tom was similar, but not the exact shade she was looking for. Just like how cousin Draco found the youthful face of Tom Riddle to be an alien moment for himself. It had all been accumulated to both his cousins Ginny and Draco to finding their separate perceptions of peace for themselves. They never fully did explain what they saw or needed, but Tom and Teddy welcomed the lazy days when Cedric came into the frame.

Nobody would ever fully know what would have happened if Cedric and Tom were alive at the same as teenagers; but it had been something else entirely that occupied Teddy's own musings. Each time he saw them both he could see the walls getting lower. Spring came, and Cedric greeted him first when Teddy went to the same corner with Cedric sitting next to Tom. The window had been opened and the curtains were pulled apart. The distance was still palpable, but he had known that Tom was the type to slowly bring others into his circle.

Something that the other Tom versions were capable too, but for other reasons and missions. (He had heard the subplot to that when his godfather thought Teddy couldn't catch his words.) That spring holiday came and went faster but when he reached ten that summer it had opened another set of memories of watching Cedric work his magic.

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"Must you two always be so jolly loud this early in the day?"

Cedric and Teddy would always reply with loud chuckling and giggling respectively as they continued making horrible jokes. Tom would look annoyed, but never too much that it would hurt Teddy's feelings. They each all knew by then that Tom had a soft side, a rare shade that Teddy wished the other Tom had been comfortable to see and feel with ease that his portrait did.

"Honestly, why I bother with you two, I'll never know."

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Portraits were not like ghosts. He had been told that. Multiple of times as he grew up. And he knew. Teddy knew.

But it still didn't stop him from wondering.

He may have been young, but Teddy loved to socialize and see every day as a new beginning and chapter he couldn't wait to start. It had been why Uncle Harry liked taking him to Hogwarts. They both shared a lot, and at the same time, were different in constitution. Magic, and Hogwarts were special to both of them, and it showed when his godfather eventually gained the job as professor for the Defense Against the Dark Arts, it had been rightfully earned and Teddy had been proud of him. His grandmother had said the same when he had been shown the room his godfather would use in September.

"Uncle Harry, can you do me a favor?"

"Sure, Teddy. What do you need?"

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"Tom."

"Potter."

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The portraits were just painting with enchantments that many artists learned how to do. Teddy had loved visiting many, and he had also loved watching the process too when he had been allowed. His cousin Ginny took up painting sometime before he had been born. He saw the rows of landscapes and portraits, some living some not. It all had been lovely, and he knew she loved it dearly.

One time she showed him a portrait of his parents that she made when he had been five. Back then, he had been memorized at the likeness and life she brought to them. But they had not been his parents, they hadn't met them their living versions, so they had been silent. Left to the imagination of how his cousin Ginny remembered them. Along with their secrets not being shared with them.

(But it had been the start of his quest.

To finding a soul beneath their lines and colors.

To each and every other painting he met since then too.)

Something about painting had become a hobby for him too. He had never been a particularly great artist, but he had fun with it. Abstract shapes had been his expertise, and the freedom to mix his emotions helped him too. It had made his cousins Draco and Ginny to also bond too. Those days when they all went to the painting room his grandmother converted, they all talked about whatever had been in their heads. Silly things, normal boring adult things and funny things.

He loved it when they made animals, or when ocean waves swirled. Each of them had made Teddy see the world they shared with him, it connected him to their hearts. Edward Remus Lupin may have been ten almost eleven but even back then, he realized something profounding. Life was wondrous, dangerous and daring. But with them passing along their wisdoms and experiences Teddy would be fine. He would seek his own adventures and answers. But all at the same time, he knew he would be loved fiercely by both his past, present and future choices and people he'd met on his journey.

Just like how Cedric had and maybe Tom.

(But he couldn't ever be completely sure. Because, sometimes his gut would fall and his heart felt like it broke. Tom Riddle was a mystery, but he had also been a boy back then. With dreams, aspirations. He couldn't have been unloved for his whole life.

Because then Teddy—because, then he wouldn't be able to stop looking at him. And wondering why. Why would the world be so cruel to certain people?)

He ventured out and spent more time seeing his godfather talking to Tom more too. It had been slower than compared to his cousin Ginny, but that had made sense she was a Weasley through and through. She was a wildfire; she always made rounds to figure her emotions and then seek solutions. His cousin Ron had said so too as well his Aunt Hermione when they heard about the times his cousin sought out Tom during the holidays. Compared to them, few people went up to Tom.

Students and faculty alike didn't pursue Tom like he and Cedric did. But it had come to portrait animals to poke their bodies to Tom's couch. (Apparently it had been a comfortable couch that many other portrait people wanted to visit.) It had been funny to see Tom shuffle with either being a good host and being anti-social. Teddy could only guess that Tom had few memories and conversations to fully understand and replicate the other Tom from 1942. It explained why sometimes his outbursts came along too.

They were ragged, and uneven when Tom had a row with Cedric. Those rare times had made Teddy sad. As if, he saw the flaws that the other Tom must have faced alone. They hurt him when Tom wouldn't want to see him too. He was sure it hurt Cedric too when they couldn't reach a hidden Tom in the castle.

It had been his godfather that spoke to him gently. The summer holiday was looming and with the letter freshly placed on top of the table Teddy couldn't mask a smile. His hair, deeply dark blue had mirrored him.

"Tom had always had a hard time letting others close to him." His hair had been tucked behind his ears. His godfather's hands wrapped him into a hug. "Portrait Tom or other versions of him alike have that same fear to an extent. That doesn't mean you should take it to heart when he said he didn't like you. Knowing the git, he must have been scared that you and Cedric are very close friends for him."

Teddy didn't let go of his godfather. "But how can someone be scared to be loved?"

The pause had frozen his own heart when he felt one hand brush away the tears from his face. Green vibrant eyes that Teddy always known and loved had that faraway look again. His glasses dropped a bit from his nose, making it easier to see the indents he had for wearing his glasses every day.

"Sometimes, love can be pretty scary. And sometimes people like Tom weren't always given the same opportunities like the rest to know how it is to be loved or to love others so easily."

"That's not fair."

"No. It's not."

Teddy's heart hurt. Even when his godfather had been close and hugged him tightly. And even though he could guess the correct answer, he still couldn't help but ask.

His head rested on the crook of his godfather's neck. "Did anyone ever love him? The one from before?"

His godfather didn't look at him directly, but he nonetheless answered quietly. "His mother loved him."

Teddy looked at the portrait of a pack of Crups. "And besides her? Were there any others that were his friends? A second family to watch over him?"

"I don't know, Teddy. I—never asked the Tom I knew if he did. He had other priorities then."

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The next time he saw Tom, Cedric had already cleaned up most of the mess. It had been cumbersome for Tom to apologize, but Teddy had been the one to understand what Tom couldn't outright say. He didn't bring up the outburst, but he had been thankful to see this Tom be loved.

It had been the only thing that helped him when he helped Cedric bring back a smile to Tom's face.

Teddy preferred that version of him. Smiling and having a light in his eyes. Portrait or not, Teddy knew that they were alive to some extent, which meant that they deserve respect too.

They returned to a relatively fun summer with Teddy catching them up. The stories they all shared were what helped him connect to them, and it showed how much of a big heart he had for anyone and everyone. It also granted him more of a firsthand experience of seeing Tom have the capacity to be free, charming and happy. The stories that he'd been able to learned from them had always been rewarding. And with Tom, it had always felt heavier but meaningful, because he knew how little Tom really revealed outwardly.

Unlike Cedric, who loved to talk, Tom was the type to hide his emotions and lessons in riddles and metaphors. Something, that could have been seen as extra and dramatic. But with Teddy, he liked the challenge. More so when his godfather came along. It had been two years, and with September coming, he hadn't hidden how much he laughed when Tom and his godfather sassed each other.

It must have been therapeutic for both. Cedric had told him so as he grew older. But when he firsthand witnessed it, Teddy knew too. That and how much everyone else eventually caved to see how much Teddy could make virtually everyone smile at his vicinity. That had been a particular reason why he had been able to keep seeing Tom and Cedric in Hogwarts when he hadn't been a student before.

(Teddy had noticed how his godfather had laughed at Tom's face from the very beginning when he saw Teddy's screaming his name in greeting. And when he chased Tom all around the castle until he acknowledged him. He had been known for being a very persistent kid since he could form sentences as a babe.)

When August came to a close Teddy saw another change to Tom and Cedric. But before he could address it, he had to leave with a brief goodbye. He would return very soon, but before that he would ride to Hogwarts in the infamous train and see what house would fit him for the next seven years.

His godfather would not be in the train ride, but he did have the luxury of having some sweets from his grandmother provided him with. His anxiety didn't fully stop him from saying hello to other first years, and other older students that recognized him from his time in the holidays in Hogwarts. It made it memorable when he spent most of that day laughing and making acquaintances and friends. It reminded him of how wonderful it felt to be eleven, and ready to learn earnestly to perfect his magic. That and it had been his chance to try out seven years without any super disasters onto his belt.

He had remembered the looks he got when most of his uncles and aunts had asked him to be careful and not follow his father, mother and godfather's luck to bring too much trouble. Or when they all chuckled when his godfather gave him a playful hug and a certain map somewhat tucked into his pocket.

Once the hat chosen his fate and the name, Hufflepuff had been announced Teddy couldn't have helped but feel his eyes water by the amount of emotions overwhelming from inside his body. From the faculty table he saw his godfather beam at him. He wobbled out of the chair but as he did that, he couldn't help but raised a fist out in triumph.

Like mother, like son his hair turned to bubblegum pink in honor of her as he sat down at his House where the other students alike smiled and greeted him. It felt like he arrived to his second home.

The rest of the way into his common room had helped when he saw Cedric greeting other returning students and saying hello to the rest of the first years. He didn't miss the friendly wink when Teddy smiled at him as he went straight to the dorm room to find his bed. He knew he was proud of him too as he took one last look at his yellow and black tie before he changed for bed.

The early morning brought a smiling Cedric with a Tom that looked both disgruntled but happy to see Teddy. He watched Tom peer at the tie and common room he had been forced to travel away from his domain. His lips twitched to nice smile, the one that made Teddy smile freely and cheekily.

"Not much of a shock really, considering how much you loved to pecked and mothered like a mother hen."

Tom sat down at a random empty portrait of a kitchen. Cedric did too when he picked up an apple. He admired it before looking at Teddy with a huge grin.

"You'll make Hufflepuff proud. I can already see it: Future Quidditch Captain and prefect in fifth year." Cedric had known about Teddy's wishes to hold up his parent's legacies.

Tom smiled more openly with the common room still empty. "Head Boy in your seventh too."

Teddy chuckled as they followed him out to the common room. Tom always had the perfect posture when he walked, but over the course of the two years he had Cedric poke at him. He had Cedric put an arm over his shoulder like what friends did all the time. It made him approachable, and human. But what he didn't expect was the soft and intimate kiss Cedric gave Tom on the forehead and cheek when they reached the entrance to the main hall.

"Ew! Come on, I'm about to eat you two." Teddy dramatically said with a fake gag.

They all knew he was happy for them. But it still had been fun to see how far Tom came when he first had arrived to Hogwarts. He rolled his eyes while Cedric amped up the dramatics with loud kissing noises at Teddy's direction first before he started to aim some raspberries kisses at Tom. Few people didn't bat an eye at Teddy having fun with two portrait people, but some of the younger generations did.

Cedric gladly greeted some of the other vocal students first while Tom stayed behind him and quietly watched both Teddy and Cedric entertain the rest.

Teddy may have not been able to meet the real Tom Riddle or Cedric Diggory, but he was fine with who he did meet. They were their own versions, with their personalized lives too. Besides, he did after all get to help the Tom he got to meet, and see this Cedric get his own happy ending too.

That was its own victory after all.