This was an idea requested by royalpinkdogs. Thanks for your review and suggestion! So it is a tad bit angst-riddled, yes, but with a title like this chapter has, you can understand why. Anyway, I hope you enjoy and as always if you like the chapter, leave a review and let me know what you think. Hope you all have a wonderful evening!

McCoy

It was the Summer he turned twenty. He'd headed out toward the west coast, eager to stretch his legs and see the world outside his Georgian backyard. He had no car of his own, so he took a bus from county to county; no real plan or route in mind. It was at a diner somewhere off the highway in Middle of Nowhere, Nevada where he met Charlotte. She was young and venturesome like him; seeking sights and sounds she'd never get a chance to experience in her small northwest town. They spent hours at that small table; talking to each other about their hopes and dreams; their ambitions and passions. They traveled a few states together, no worries or attachments to hold them back. They were carefree; not bound to any responsibility but their own obligation to make the most out of each and every day. Eventually, the future loomed and McCoy knew what he wanted to do. He wanted to study medicine. To help people. And he certainly couldn't do that traveling the country as he was. Their departure was bittersweet, and they didn't exchange contact information. They knew the odds of their ever crossing paths again were slim. Better to remember the past as it was than struggling to chase it once it was gone. He never did see her again, but he remembers that Summer as one of the best of his life.

Kirk

He wasn't exactly the poster boy for monogamous relationships growing up. He never got attached; never really looked for anything more than a few days of fun. A week tops. When he first met Anya, he didn't except anything different. She was beautiful; dark hair and a set of deep brown eyes to match. He spotted her sitting in an empty corner of the pub he frequently visited in search of one-night stands. He'd flashed a smile, tried his charming banter shtick. She saw right through it all. Something about that, the way she didn't just go along with his immature, boyish antics-how she was there to balance him with her soft demeanor-is why he liked her so much. It worked for a while; he surprised himself with how much he enjoyed having a constant presence in his life. But, like most things at that time for him, it didn't end well. He was still a drifter; didn't really want to stick with anything. He was a repeat offender who got into trouble with the law just a bit too often. His lack of ambition is why she eventually said goodbye and never looked back. Every now and again, he thinks of the person he's become-of the passion he's discovered since joining Starfleet- and wonders how things might have been if she'd met the man he is now.

Sulu

Before he discovered his love for flying-back when the only thing that mattered to him was living life carefree and happily-he worked as an extra hand maintaining the boats on the San Francisco Bay. It was a casual arrangement; he knew a good number of the sailors who docked there often, so he helped make repairs and patch jobs when they needed them. The pay was good and some of them even let him take a boat out on the water every now and again. It was on a day when the sea was rough and the waves washed forcefully aboard the boats that he spotted an overturned kayak bobbing along the current with a body struggling desperately to clutch it and stay afloat. He took a small fishing boat and paddled out to the overturned vessel. It was difficult through the rain and rough waters, but he managed to pull the person aboard. His name was Will and he had stark blonde hair and blue eyes that Sulu found himself quite often distracted by. Will spent the night on his couch that day, and stayed many subsequent nights after that. They sailed everyday; going far out beyond the bay and the confines of the shore. They'd dream about traveling the world on the sea one day; together of course, Sulu always joked that Will would have died if it hadn't been for Sulu's heroism. But it was only ever that: a dream. Sulu left for his first semester at Starfleet the end of that year. From what he knows, Will moved across the world; somewhere they'd once talked about seeing. Bermuda or Antigua maybe. He supposes that, in the end, they both achieved the dream in a way- Will traveling the world and Sulu, the galaxy.

Spock

He had very few people in his life on Vulcan that he would have considered "friends". He was an outcast for most of his adolescence; his father called a traitor and his mother shunned for her identity. He was the product of a marriage ostracized by his own people. Most days he was lucky if he returned home without any harassment from the other children. His mother had always taught him about love; the human capacity for it and its curious lack of a consistent definition. Love is different for everyone, his mother had told him. Spock didn't quite understand this growing up, but he supposes now he did know love in his own way. He loved his mother. He loved his father. And looking back, he believes that he did love another. Her name was T'ma, and she was one of the few vulcans outside his family who saw him as an equal. They studied together after classes and spent many nights mapping the stars. His pet sehlat did not feel threatened in her presence as it did so many others. She was, and will forever be, the first friend he ever loved. Each year, on the anniversary of his planet's destruction, he makes sure to light a candle in her memory. His only regret is that he never thanked her for all that she gave him in a childhood so void of happiness. He honors her now by building new friendships; by loving others and receiving their love in return.

Chekov

Remembering her is difficult, but not because of their time spent together; no, those were some of the best months he's ever known. He ran away from home at fifteen and enlisted in Starfleet the second he got the chance. He was the youngest, of course, so he had little in the way of companions that first semester. Most people didn't give him the time of day, and if they did, it was usually endearing teasing over his youth. Ruffling his hair or something unbelievably annoying like that. He turned seventeen his second year at the Academy, and it was on the night of his birthday, as he sat in the library-alone-studying for an exam, that he met Scarlett. She was the daughter of an admiral, newly eighteen and looking to enlist in Starfleet within the year's end. Her laughter made his heart flutter and he can still remember the first time he built up enough courage to give her a quick kiss on the cheek before saying goodnight. She helped him learn English better. She was patient and kind; she didn't grow frustrated when he'd fumble words and trip over unfamiliar letters. He taught her how to cook an immaculate pot of stroganoff and they'd spend late nights on the couch watching old movies together. It is still difficult though; to remember her. She was sent on her way to Vulcan that day as well, but her crew was not as lucky as his. The memorial was long and her name felt foreign to his ears as it was read from a list of men and women taken from life far too soon. He remembers her though. So often when he finds himself unable to properly pronounce words and phrases like his authorization code, he can hear her voice softly guiding him through it; telling him to take a breath and speak slowly. That it's okay. One day he'll get it. He just has to keep trying.

Uhura

He was her most cherished friend. Addae was the son of her father's coworker, so they saw each other quite often as children. They did everything together; reading, learning, exploring. And especially causing mischief on the days their fathers brought them both to work. They were attached together; one was rarely without the other. Eventually, their childhood friendship became something more, and their newfound relationship was a time of pure joy and exuberance for them both. She made him happy, and he in turn did the same for her. Their love was rooted in a friendship forged through endless nights of stargazing and storytelling. There was a time when she very well thought he was the one; the person she believed she could see herself sharing a life with. But as they both grew, so did their ambitions. In turn, their future was no longer a singularity, but rather split between their differing passions. He joined a humanitarian organization and left to travel the galaxy in search of ways to improve welfare across the universe. She enrolled in Starfleet that very same day. He's married now, even has a small child of his own. They don't talk nearly as often these days. But despite the distance, they never forget the memories they shared. They cherish the friendship that helped the other grow into who they are today.

Scotty

The second he turned eighteen, he blew out of his hometown like the summer storms that so often quenched the Scottish countryside. It wasn't that he didn't enjoy his life there; he did. But he knew the world had more to offer. He started small, traveling across Europe and visiting the various countries he'd only ever read about. When he was satisfied, he hopped a shuttle to America and eventually worked his was across its many states; their names all blurring together as he passed through them. He reached San Francisco, California one foggy morning in the spring. He staggered off the train he'd taken from Arizona tired and in desperate need of a place to sleep. He somehow stumbled upon a tiny coffee shop sandwiched between an apartment complex and a towering office building. There is where he met Catherine; a red-head with soft blue eyes and a smile that made his knees weak when he first walked through the door. She offered him her couch and a job at that very same shop. He gratefully accepted the offer and within a few months, they found themselves the dynamic duo of coffee craftsmanship. He'd dated before, but never felt the way he did with her. He almost found himself perusing the ring section of a jewelry store one sunny afternoon, but that notion was short-lived. He knew he couldn't stay in one place forever; that just wasn't who he was. He went on his way, with her blessing, and soon he was halfway across the galaxy; far, far away from the life he might have had. He hasn't talked to Catherine in years, but he likes to hope she's doing well; wherever she may be.