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Kurt was still very young when he decided that he wanted to become a star on Broadway. Or go into fashion, depending on what day of the week it was that you asked him. He never quite lost sight of that dream, not even when his mother fell ill and then died, leaving Kurt and his dad behind. It had been a hard time for both of them. Once when Kurt had woken up at night and heard his dad crying downstairs - quietly, always so quietly so that Kurt wouldn’t hear, wouldn’t be subjected to the massive pain crushing Burt because he was Kurt’s dad and he had to be strong for his boy because it was only the two of them left now - he’d seriously thought about giving up his dream because how could he leave his dad behind? He would be devastated if Kurt left him too.
It spoke to the special bond Kurt and his dad shared that Burt, upon hearing Kurt talking about starting to work in his dad’s garage when he grew up - Kurt who at the time got a mild panic attack if he even looked at greasy machinery wrong - sat his son down and explained to him that no matter what he ended up doing, no matter where it would lead him, he would always want Kurt to pursue his own dreams. Suffice to say, Kurt’s reluctant thoughts of becoming a mechanic in order to stay with his dad died a swift death right then and there.
He still started helping out his dad in the garage though. And years later, when puberty hit and he had to come to terms with his sexuality, he was glad that he and his dad had reached an understanding that enabled them to be open and honest and easy with each other. Plus, Kurt probably knew more about cars than your average football jock ever dreamed of knowing, so there was that.
High school had been a tough time. Not only was there the big revelation that, yes, Kurt not only looked fair and gay, he actually was gay too, and quite openly so. He also had to deal with unrequited crushes which, years later, brought an embarrassed laugh out of Kurt because of the creepy stalker-y tendencies he’d developed but had seemed so reasonable at the time. Luckily for everyone, Kurt got over his crush on Finn eventually. And it had brought Carole and Burt together, and Kurt could never regret bringing a new love into his dad’s life.
Then there was the bullying, of course.
Kurt never quite found out why Dave Karofsky had targeted him specifically, not letting up even a little bit. He’d made Kurt’s high school years a living hell and the only thing keeping Kurt going was the thought that one day he would be out of these halls and this small-minded town and Dave Karofsky would probably end up working at a gas station while Kurt Hummel dazzled New York on Broadway. Kurt was glad that he’d never been weak in mind or resolve - you only had to ask his dad to get confirmation how pigheaded Kurt could be if he wanted to - or the bullying and constant verbal threats might have driven him to suicide. As it was, he never quite saw the point in ending your own life to escape because really, wouldn’t that make the bullies the winner? Kurt would never let them win.
And anyway, he had his friends in Glee club and, weirdly enough, the protection of Sue Sylvester, which made being shoved hard into a locker or being dowsed in icy cold and sticky slushie not exactly okay, but at least bearable.
And he had his dad; his dad who would do anything for Kurt, who would stop the world from rotating if that was what Kurt needed. It was that thought that kept him afloat until graduation.
His graduation year was... rather eventful, all things considered. For one, the New Directions won Nationals that year. The competitions leading up to it had been tough as usual, though The Dalton Academy Warblers didn’t compete that year, something about their soloist dropping out or something, the rumor mill never quite made it all the way back to Lima.
Kurt also met a boy over the internet.
Okay, that sounded sleazier than it was. They met in an online forum where gay teens talked about their coming out stories and the harassment they went through on a day to day basis. Kurt stroke up a friendship with this quiet boy who seemed to know exactly what to say to make Kurt feel better. After several weeks of chatting back and forth, it was revealed that he didn’t even live all that far away and really, the gay teens of Ohio had to stick together. Plus, Nate turned out to be a put together, honest guy who was on his high school soccer team. It was probably his height and his well defined muscles that prevented him from being physically bullied, but he had his fair share of threats and weird reactions from former friends. In short: Kurt knew what Nate was going through and vice versa, so when they met in person for the first time, they knew what to expect of each other.
Nate was his first kiss, held hands with him in public, and generally adored Kurt, but they both knew that they were not meant to be together for the rest of their lives. Nevertheless, Kurt had to sit through an embarrassing sex talk with his father who, upon reflection, had told him exactly what he needed to hear in order to grasp how important sex was. And while Kurt had learned more about positions and kinks over the internet - way more than he ever cared to learn, come to think of it - he appreciated that his dad wanted him to know these things, especially if there were two guys involved thinking with their dicks.
He talked about it with Nate, who blushed profusely and then admitted that, while he thought about sex all the time - which teenage boy didn’t, really? - he was nowhere near ready to act on it. Kurt had agreed; while he knew the mechanics in theory, he had horrible visions of being terrible at sex and really, for him it had always been more about the romance and flowers and hearts than the physical. There was, after all, a reason why he adored musicals.
Needless to say in the end, his teenage hormones caught up with him, and while he knew him and Nate were not destined to be together forever, he trusted him with his feelings and his body. So, Nate was his first, long before prom night because Kurt was not that tacky, he would lose his virginity on his own timetable thank you very much. And while it was not earth shattering and hurt a bit, it was still nice and he felt secure and treasured in Nate’s arms. It wasn’t a surprise to anybody when Kurt and Nate called it quits a few weeks before graduation but decided to remain friends. Such good friends, in fact, that they were each other’s prom dates and had a good time flipping all the bigots the proverbial bird by attending together.
While Kurt had made his first tentative steps into a relationship with Nate, Finn and Rachel had a major row and broke up. It was so epic, in fact, that high school kids were still talking about it five years later when none of them were at McKinley High anymore.
Nobody had ever gotten any specifics - except maybe Carole because Finn told her everything - but for weeks they couldn’t even be in the same room with each other without Rachel bursting into tears or Finn looking like his mother had died. It put a severe strain on everyone and it was sheer luck and the fact that Rachel was, above all else, a professional, that got them through Sectionals.
Kurt was stuck in the middle for all of it. While he didn’t know what had happened, he could see that both of them were hurting. So he tried to be a good friend for Rachel while not betraying the brotherly code he had with Finn, which was a tightrope walk most of the time.
And then, like a storm passing through, they stopped ignoring each other. For the next few weeks, they had awkward, stilted conversations where Rachel talked too much and too fast, and Finn spewed out even more moronic than usual crap. It was really rather painful to watch. But after a while, the awkwardness faded, and somewhere along the lines, they became friends. Kurt had never been sure if they had ever really been friends before they became an item. Suffice to say, it worked much better for them in the long run.
(Years later, one night while drunk off their asses after celebrating Rachel getting a leading role in a Broadway musical, she confessed to Kurt that she’d been pregnant and, without consulting anyone, got an abortion because she couldn’t, she just couldn’t be Quinn version 2.0 and really, how could she ever be a mother at 17, right? Finn had been furious when he found out and for a long time, Rachel had thought he could never forgive her for effectively killing his child. So she was so glad, Kurt, so glad he had found Jenny and that they had a little daughter now and they were so happy, right?
The next morning Rachel didn’t remember their conversation and Kurt pretended he didn’t either, but sometimes he closed his eyes and saw the sad, wistful look in Rachel’s eyes when she’d told him that she couldn’t be a 17 year old mother, and would spontaneously call her to meet up for coffee. She never quite knew why he did it, but she was grateful all the same. Their friendship was strange but it worked for them.)
Moving to New York, leaving everyone and everything he knew behind - it was harder than Kurt had ever imagined it would be, even though he knew that at least Rachel was just a phone call away if his homesickness got too much and he needed someone familiar close by not to lose his mind. And he missed his family so much. Logically, he knew that his childhood fears of his dad staying behind all alone were no longer valid because now he had Carole and Finn who wasn’t going anywhere anytime soon. Still, for the first month he called home almost daily, talking to his dad for hours - his dad who didn’t like talking on the phone on the best of days but missed his boy so terribly that he’d rather just hear him breathe through the line than not hear from him at all.
It got a little easier, eventually. Kurt’s college courses picked up speed and he had rehearsals and auditions to get to.
Then Finn fell head over heels in love with a young woman named Jenny who was training to be a nurse. She was lovely and the complete opposite of both Quinn and Rachel, which incidentally made her perfect for Finn, who needed someone who balanced him out. It didn’t even take them half a year before they were married, and barely a year after that they had a daughter.
When Finn and Jenny told them that they wanted to name her after Kurt’s mother, Elizabeth, both him and Burt didn’t know what to say. Needless to say, they were both touched and there were many hugs and kisses. Plus, the girl was super cute and Kurt adored her the minute he was introduced to the tiny little being who was now bearing his mother’s name. He was sure that she would have approved.
The first year after graduating from college, Kurt had drifted from one small role to another, never quite what the producers were looking for but assuring him that he was good, just not suited for any role currently on offer. For a while Kurt battled with disillusionment, seriously thinking that maybe he should give up his childhood dream, try to get a foot in the door in the fashion industry. Instead, he went back to college for his Masters degree.
Being in school for another two years helped him overcome some of his issues he’d developed after being rejected over and over and over again. He still applied for roles but could shrug it off better when he was rejected. He practiced his screen writing skills instead, thinking that if no role was out there for him he would damn well write it himself.
With a Masters in his pocket and more confidence than he’d had two years before, he started auditioning again in earnest while working as a substitute teacher in a high school, managing - of all things - the Glee club. Then a small, independent theater offered him a leading role in a small production, which got him noticed. When Kurt turned 27, he had reached the goal he’d set when he was still a boy in his childhood home: singing on Broadway. He was still not the crowd-stopping star of any production, but people had started to notice him more. People had started to think about writing roles just for him. All things considered, that was pretty stellar.
And then his understudy tripped him and Kurt sprained his ankle.