Author's Note: This is in response to something of a challenge put forward by killersharky on Television Without Pity. It was proposed that "Five Things" fics should be done, to unblock those with writers' block, and to encourage those who haven't yet written.

This is my contribution to the cause: The Five Women that Chuck has Loved

5) Mom

She left when he was so young. Fifteen years old, just a sophomore at Harvard-Westlake. When Ellie told him, he tried not to cry. He really did. But there he was, in the middle of his teenage years. His dad had left them years before, and now his mom was gone too.

He alternated between missing her desperately and wanting to hate her with every fiber of his being. It was horrible. No fifteen year old boy should have to endure that.

The Bartowskis had never been a particularly religious family. But Chuck found himself on his knees, night after night, praying to a God that he'd never really known, never really understood, asking Him to send his mother back to him.

Sometimes, he would fall asleep during his prayers. But other times, he would break down into sobs – tortured, wailing cries, asking "WHY?!" And yet, the answers would never come.

4) Ellie

More than anybody else, Ellie has been the most constant person in Chuck's life. He's seen pictures – she was there when he was born. She was there when he was christened (at their grandmother's insistence). She was there on his first day of school.

She was there when Peaches died. He remembered it so clearly. Or at least he'd thought he had, until that day not too long ago when she informed him that that was actually the SECOND Peaches.

But that just made him love her even more. The fact that she had been so concerned for him that she'd conspired with their mother to replace the original with an identical dog so that his little ten year old heart wouldn't be crushed.

On the day that their mother left, Chuck could see the hurt in Ellie's eyes. He could see the desperation, the horrible pain. And yet, she remained steadfast – the anchor in the storm of Chuck's teenage years.

She was there when Stanford expelled him. When Bryce stabbed him in the back – not once, but twice. When Jill dumped him. When Sarah and Casey came into his life and created a maelstrom of insanity. When he fell for Sarah, too hard and too fast.

Ellie was always there. She was the constant in the equation of his life.

3) Jill

During the fall semester of his freshman year at Stanford, Chuck was convinced that Jill was the best thing to ever happen to him. She liked computers, and she liked him, and he liked her right back.

It had all the hallmarks of a textbook college romance – the late nights at Denny's, the ridiculously long conversations on the phone when they were apart, the AIM conversations they had when they were but a five minute walk from each other. They both dove into it headlong, never stopping to consider what might lie ahead.

When Chuck went home for Christmas in 2002, Jill went with him. To all outward appearances, they looked so happy. Heck, Chuck was certain that they were happy. In fact, as he confided to Ellie on New Year's Eve, he was saving up some money so that he could buy a ring – and ask Jill to marry him.

And then, Chuck's entire life got turned on its ear. Three months later, he was expelled from Stanford based on fabricated accusations by his own roommate and the man he thought was his best friend, Bryce Larkin. But then it got worse. Two weeks after the long train ride home to Los Angeles, he received a letter from Jill.

It said she was sorry. It also said that it was over. And it said that it was because of Bryce.

And the worst part of all was that Chuck was still deeply, insanely in love with her.

2) Kaylee Frye

Okay, so she was a fictional character. Chuck didn't care. She was still an amazing woman.

After all, here was this girl, about Chuck's age, who had no pretensions about herself, who was, in fact, a complete and total geek, and who by everything she said on the show, really liked sex. Chuck could definitely go for a girl like that.

Too bad she was a figment of Joss Whedon's imagination. Too bad Chuck would never have a snowball's chance in hell with Jewel Staite – and he knew it. But that didn't stop him from having a huge crush on this fictional character.

He mentioned it in passing to Jill once, and she thought it was really weird. Chuck didn't quite understand that – after all, she liked "Firefly" too and had on more than one occasion made rather lewd references to the tightness of Mal Reynolds' pants. But she said that was different.

Chuck didn't see how. And after Stanford and Jill both dumped him, Kaylee got him through. He watched the DVDs over and over again. He even wrote some fanfic where he put himself into the story, just to create situations with Kaylee. It never saw the light of day.

And when Serenity came out, he just about leapt for joy – and then booed LOUDLY at the end of the film, when Kaylee hooked up with Simon. Fortunately for him, he wasn't the only one in the theater booing.

1) Sarah

When the tall blonde woman with the piercing blue eyes walked into the Buy More on September 25th, 2007, Chuck was at a very low point in his life. Four and a half years had passed since Stanford. He just didn't seem to have the motivation to continue on with life.

Ellie saw it. She tried to be supportive, while at the same time, trying to kickstart Chuck's life. That's why she threw him a birthday party six months after his birthday. She desperately wanted to see her little brother make something of himself.

But from the moment Sarah Walker introduced herself to him at the Nerd Herd Help Desk, his life had nowhere to go but up. The first time his eyes really registered her, his brain just about melted. Then, she flirted with him, and he just about died from shock.

When she asked him to take her around the city, he was afraid to blink, lest he open his eyes and find himself singing with the heavenly choir. He thought that finally, FINALLY, his life was turning itself around.

And, well, it was. Just not quite the way he expected. When he discovered that Sarah was a spy who had been shacking up with Bryce Larkin – well, it kind of rankled a bit, especially the part about Bryce.

But the more time he spent with Sarah, the more she seemed to get him. She understood Chuck, understood his motivations, even tried to understand the geek part of him. And though she had trained herself not to admit it, she really started to like him, and he could tell.

He couldn't help but like her right back. She was beautiful, she was kind, and despite the layers of deception that she had to live with for her own protection, he could tell that at her heart, she was a genuinely good person. And he liked that, a whole lot.

When she told him that their not-a-relationship was never going to lose the "not-a" tag, he was crushed. But he saw things in the days following that made him think twice – she cast dirty looks at Lou; when she stormed out of the Buy More, it was just a little TOO convincing; and when she came into Club Aries, she had a look on her face that said she was absolutely terrified for him.

And that, of course, all culminated with the kiss at the San Pedro Docks – promptly followed by Bryce the Bastard returning to screw up Chuck's life - AGAIN. He had watched, helplessly, as Bryce's return had caused Sarah to close herself off to ALL emotions. It had taken a murdered alarm clock and a promise of friendship to get her to open back up just a little bit.

But the clincher – the little, tiny sign that made Chuck realize that he truly loved Sarah Walker – was that night on the helipad. The night after the Buy More was cleaned out. The night that Longshore came to extract him.

When Sarah came to the helipad and was begging Longshore for more time, her right hand carefully slid behind her back. Chuck knew her too well. He knew that her right hand never went behind her back unless she was planning to draw her gun. And that astonished him. The fact that she had been planning to draw down on a fellow agent, to risk her career, her own life, for him.

When he held her hands and said good-bye, he watched her eyes fill with tears. But that wasn't all he saw. He saw the look behind her eyes. The love there. And despite the fact that he thought he was about to be moved into a secure government bunker… seeing that in her eyes made his heart sing with joy.