Exactly one week after he left, Dean returned to beacon Hills to help make funeral plans for his friend Derek. He stayed with his Uncle, until the actual day of the Funeral, and after that he Enlisted Peter, to help him to once and for all lay to rest that Argent bitch.
Peter raged, and cursed at the world, and eventually shut everyone out for the week leading up to the Funeral. Only Dean could pull him out to eat, and even then Peter raged, and with every too hard punch and annoyed growl Dean just accepted it, knowing he deserved the punishment. Peter with all his plans, and schemes, and power to push people around, he couldn't even save Derek. He knew their life was Dangerous, but Derek was pretty much innocence personified. Peter doubted he would ever in a million years find someone as pure hearted as Derek. So he helped Dean get their revenge, and started up a Publishing company in the months to follow, that only published children's books and every single book was dedicated to Derek.
August 17th 1995 Derek Met Jaqueline Baker, who moved into town suddenly, and just as quickly fell in love with Derek Matthews. When School started, no one could accept their summer love, and soon rumours about the girl who stole Derek's heart were flying throughout the school every day without Fail, someone would call her a slut, or a gold digger, Derek lost a lot of friends when their only response to his question Why do you think she is using me? Was just a Because.
Through all this Jaqueline held her head high, she was raised a hunter, and she was a hero, of course only she knew this but still it kept her head high, and her back straight. Derek only saw the Grace with which she dealt with the onslaught of bullying and asked himself, why did this amazing Girl deem me worthy of her attention?
On October 4th 1995 Derek Matthews found out he was going to be a father, him and Jaqueline decided to keep it quiet until they figured out if she was going to have the baby or not. Two weeks after that Derek asked Why not? His parents were Teen Parents, and they made it just fine. So the two decided to keep their baby.
When Jaqueline started showing and even Derek's larger shirts were getting a little tight on Jaqueline , she decided it was high time to drop out of school, her school career was pretty much in the dumps anyway with her moving around all the time, but there were new self-paced homeschool programs that she could definitely do. Except with her dropping out of school, came telling her parents that she was pregnant, and will not be raising her child as a hunter. Surprisingly it was the refusal to raise her child as a little soldier that got her kicked out of her home than the actual being pregnant part. Jaqueline found herself welcomed into the Matthew's house with open arms and a lot of support to help her finish school to at least get her GED. The Matthew's Family all asked themselves why any parent would reject their own child?
Derek's good friends David and Margaret dropped by for a visit after three years apart. It was a whirlwind visit with David and Margaret explaining that David's father has given him a job in the family Firm without even being accepted into law school yet and therefore buying them a house in beacon hills, and Derek introducing them to his Girlfriend. Which ended up with Margaret tearfully congratulating them, then explaining they found out they couldn't get Pregnant. This left Derek wondering, why such loving people couldn't have a child, while some were willing to just throw their child away? Derek might still be holding a grudge against the Bakers.
The Matthew brothers were ecstatic, with their age difference Derek knew that they could be in the buddy programme together, if he worked hard to be in AP classes and one of the top students in the school. Today, the brothers found out they weren't only in the programme together but buddies. On the first day, Derek met Dean Winchester, and Derek Hale, Dean he heard about, he moved just before the school year started, all the girls, even Jaqueline stared at the pretty boy. Jaqueline said her staring had nothing to do with his looks, okay maybe a little, but more to do with her Family's business. The family business that was never talked about, and apparently Winchesters were practically famous. That was all she was willing to say and Derek never asked further. Dean's little buddy, Derek Hale was Famous as well, well his last name was. The Hales were a well-respected Family, pretty much Founders of Beacon Hills. With every marriage and Child the Hales had, their wealth grew with them. They were slowly developing Beacon Hills into a city by buying up all of the industrial district, and turning it into an urban area. Listening to them talk at lunch, and observing them throughout the day, Derek asked Why he never got the nerve to talk to Dean sooner? Well either way, he could update Jaqueline about Dean's actions, even though she stopped scanning newspapers a while ago (she started after Dean arrived). Derek decided not to ask her, why the newspapers needed to be scanned so frequently…. Or viciously? He knew that wouldn't end well.
The announcement of the Dance, and the fact that the buddies were hosting it, led Derek to automatically going with his brother, or Jaqueline, hopefully both. So when Rumours of Dean going with Peter went around the school like wild fire, Derek was maybe hoping for them to be true, because a gay couple would be a slight more scandalous then a teen pregnancy. So he may have made up stories, and embellished other known stories and facts with their names. Derek joyfully watched as people ate up his words, and took them further. Soon Peter, and Dean were in a secret love affair, it's why Dean is so flirty, yet aloof when it came to the fairer sex of beacon hills high. Derek peppered the rumours with random sightings and catching them unawares a few times, all in good fun of course, never expecting that the outcome would simultaneously start and essentially end bullying against anyone identifying as part of the LGBT community in Beacon Hills High for many years to come. The famous conversation between a fifteen year old and five adults plus two snotty teens, turned into a myth that if you bullied anyone for being gay at Beacon Hills High your entire life would be ruined. Derek, wondered why people thought that love could in anyway be disgusting? Derek, also wondered why he never got his comeuppance, for his part in perpetrating the rumour mill.
After the Incident, Derek and Dean started up a friendship, Dean loved his theories of the people around him, and Derek prided himself that he actually got Dean to laugh once or twice. Derek Hale was enamoured with his stories about Dean Being a hero, or a secret Prince from a foreign country. Apparently being friends with those two came Peter Hale, who indulged his Nephew's whims, and whispered to Dean with a smirk on his face, making the older boy laugh or grin, Derek knew his stories may have been fake, but there was definitely some truth to them. So Derek was happy to host Dean Winchester at his house to actually make decorations for the dance. Derek may have also, liked his Girlfriend losing a bit of her stoicism when he told her Dean was coming over to the house, if it took another man to make his girl smile like a loon then Derek will gracefully bow out of the way. Derek literally got out of the way for about an hour, because he wanted to make dinner for everyone allowing the two to talk. This was like one of the top best ten decisions he ever made, because somehow Dean Winchester got his girlfriend to go to the Dance. Derek very smartly never asked why she agreed to go to the dance when Dean asked her. But he did ask who Claudia was, and why she had her number clutched in her hands like it would disappear. The answer made Derek think Dean was the greatest human being ever, Jaqueline told him it was the number of the woman who helped Dean's own mother when she was kicked out of her house when she was pregnant with Dean.
The night of the Dance left Derek with many questions, the biggest one was why was Peter, interrogating him about his life plans and frowning more and more, until peter pointed at Jaqueline and said 'you need to take care of them, Family is so very precious Derek, and life is so cruel, So we are sorting out your life tomorrow weather you like it or not.' Derek wide eyed wondered why peter hale a kid two years his junior, and quite frankly never shown any interest in him before was so worried about his girlfriend and their child.
The next day led Derek to the Bank, where he heard the Rumours amongst the adult population of beacon hills, saying how that little hussy trapped Derek in a relationship, how she ruined his future, how his life was over. Peter seemed to be memorizing their faces, and Dean glared so hard he actually made someone squeak in fear. While the outing on a whole was beneficial, Derek was left wondering why people are so idiotic, even his little brother Kyle knows it takes two to make a baby, and yeah he's not going to college, but that's his choice. Derek wondered most of all though was why they thought it was any of their business. Pushing that out of his mind, Derek felt pretty accomplished that day, knowing his child will go to loving parents if anything happened to him and Jaqueline. No one questioned why the Whitmore's were chosen as godparents, it was a very smart choice.
When the school year ended, Peter dragged him from his first full day of work to send off Dean, who apparently was trying to mimic a zombie, with the bags under his red rimmed eyes. Derek didn't ask where he was going, or why he was leaving, from the little he gleaned from Jaqueline moving was part of the family business. He watched as Dean hugged every member of the Hale Family, of the 9 only 2 he knew, but he was surprised when Dean hugged him, and handed him a necklace, Dean said it was for protection for Jaqueline and his baby. Dean made Derek promise that he would make her wear it all the time, before he let the necklace go and allowed Derek to take the full weight of it. Holding the object made Derek believe that this thing could protect Jaqueline from everything. Derek watched Dean drive off and asked why he was so special to gain such amazing, and odd friends? Derek placed the necklace around Jaqueline as soon as he got home, and she stared in awe of it, before asking where he got it from. Derek just said Dean, and he wanted to ask why the mention of his name made her look sad instead of happy for once, but he didn't because it was probably the same reason why the Hales looked sad, not knowing he himself looked exactly like the others. Jaqueline kept the amulet, as she called it not a necklace, on her at all times, but never wore it after the first day, saying it's for their baby.
Oh god Derek was in a panic, he was running around the house, while his Mother helped his Girlfriend to the car, and he tried to remember where the baby bag was. Asking himself why he didn't listen to his girlfriend when she told him to just leave it in the car, when his mother came back in and said, she put the bag in the car last week. Derek grabbed his keys and ran to the car to drive his girl to the hospital, leaving him wondering, why is she so calm? 'Baby, we have time, the hospital is close, and it only just started' Jaqueline answered reading his face perfectly. As Derek drove, he placed a hand on his girlfriend's stomach and could feel how strong she was could feel her muscles cramping, as a contraction hit, she just shook her head at his worried face, and clenched the amulet in her hand and breathed through the pain as he let go to drive with both hands on the wheel, Derek once again asked why was he so lucky to have found the love of his life so soon?
Derek hit a wall of Terror, there in the middle of the road was a woman as translucent as ever, Jaqueline screamed for the first time, and she told him not to stop driving. Derek closed his eyes, expecting a hit that didn't come, didn't notice the woman in the back seat of the car until she had her arms around his neck, he tried to keep control but the car had a mind of its own sped up and it flipped over as they swerved into a ditch. Derek watched in horror as his girlfriend clutched at her stomach before everything disappeared, and Derek asked himself as he woke up in bed why did he have such a horrible Dream, when a person popped out of nowhere and explained he was dead, and it seemed his soulmate would be arriving soon, "I am so sorry Mr. Matthews."
Derek watched in horror as his girlfriend taunted the thing that killed him and tried to kill her with a smirk on her face, as she waited for the ambulance that seemed to take forever. Why was it taking so long? He watched as they cut his son out of her belly, because she refused any treatment until her child was born, Derek waited what seemed like forever to hear his son cry, and poor beaten and bruised Jaqueline Clutched the Amulet in her hands and demanded the nurses to see, and let her hold her Child. The nurses gave into the dying woman's request and Jaqueline placed the Amulet on her not breathing child's chest and breathed her last breath that held every hope she had into his lungs, and he cried. Derek watched as his girlfriend died with her child in her arms and the nurses cried as they picked up Baby Baker from his girlfriend's lifeless body. His mother rushed in and collapse to the hospital floor, the second she registered the flat line over the baby's cries, with the most horrible of cries of her own repeating the words 'No' and 'Why?'
Derek greeted Jaqueline as she woke up much like he did, and they mourned the life they never got with their son. 'I held him' she finally said, 'I know' he didn't ask why he never got to meet his son.
The couple watched as the Town asked why? The Whitmore's asked why their custody wasn't contested by the Matthews family. Dean asked why he didn't trust his gut more. Peter asked why he couldn't do more, and deputy Stilinski asked why he felt an odd sense of dejavu over this tragedy, feeling immensely sad as if he went through this personally before.
The Whitmore's found Mr. and Mrs. Matthews on their doorstep, with a bundle in their arms. "He doesn't have a name yet, except baby Baker." The Matthews handed over their grandchild, with a sad smile. The Whitmore's invited the couple in, and cried over the tragedy sparking an idea from Margaret.
"He will be names Jackson, after his mother, Derek after his Father…"
"…and Whitmore for you who will love him" Mrs. Matthews finished. Her voice booking no argument. "But I want to visit my grandbaby anytime I want" to which the Whitmore's agreed instantly.
The Funeral was Held that Sunday, and every hale showed up, and majority of the town that once scorned the young couple, and they all asked why, were we so cruel. After his parents said their good byes with a clod of dirt for them both, a lily for Jaqueline, and a rose for Derek thrown onto their white coffins. The town was surprised that the next in line was Derek Hale leading his Uncle and Dean, with a sword in hand and a paper crown on his head, threw his bit of dirt in Derek's grave first and then the sword telling him that he was the most Nobel of knights, and he was a true Hero until the end repeating the words he said at the night of the dance, Dean threw a mixture of salt, Iron, holy water, and mountain ash instead of the traditional clod of Dirt, and Peter threw a wolfs bane flower he plucked from the bouquet he held with apologies of not telling Derek Matthews about the supernatural, thinking they were protecting him. Derek then led them to Jaquelin's grave, where he took the rather large bouquet of flowers from his uncle, where he said a simple goodbye and said she was the prettiest queen he ever saw, so she deserved every beautiful flower ever" this made Mrs. Matthews thank him for his kind words, and once again Dean and Peter followed suit with the odd mixture and the purple flower except for Jaqueline, Peter had three flowers twirled together and a spiral token tying them in place and to Jaqueline they promised revenge, and protection of their baby, Dean also promised a proper hunters burial for both of them should the need arise.
After the Funeral Dean spent another week in beacon hills looking into every car accident that happened in town, Peter helped out and narrowed it down with his knowledge of the Hale curse. Dean found one name, Eva Argent, who was the matriarch of the Argent family some 200 years ago, her brother married into the Hale Family never agreeing with his Families ideals, Eva in a fit of rage, when she found her brother who she thought was dead was actually living with the Hales, tried to kill his pregnant girlfriend the plan back fired and she ended up dead by the road side. Soon after the Hale curse was in place, but not so much a curse as a vengeful spirit, who killed anyone who was pregnant that held knowledge of the supernatural world traveling on the roads of Beacon Hills. Dean with the help of Peter dug up her grave, and salted and burned the body. Giving Peter his first practical lesson of hunting.
Peter felt that no one should forget Derek or Jaqueline, and started a charity to help troubled teens in Jaqueline's name, the hidden side of the charity helped young teens who wanted to leave the hunting life. Though it took months Peter also started a childrens book publishing company and every book published was dedicated to Derek: who never stopped telling stories.
The couple watched, and once their time viewing the living was up they were done with Why's?