The two of you have had a confusing "friendship".
It all started when you were adopted by Marillia and Matthew Cuthbert. You had come to Prince Edward Island from America, after being in an orphanage all your life.
You then started going to school, making a few friends. Specifically Diana, she was your current best friend. Originally, you had completely ignored Gilbert, despite him trying to get your attention. Ruby had liked him, and Ruby was your friend. You didn't want to make her sad, even if you did know that Gilbert would probably never like her. He didn't seem like the type to date, despite how dreamy he was with his dark brown curly hair and brown eyes.
You had even hit him in the head with your slate, which only made him more interested in you despite your efforts to try and push him away.
One day, while walking home, Billy Andrews just had to mess with you. Gilbert saw it, and made him leave you alone. You didn't know why, but ever since then you had grown a liking to Gilbert Blythe, despite the past rivalry and banter.
But you two couldn't be together. You had promised to never date him, and he was so well known for never dating. Not to mention, you two were complete opposites. But the way he constantly looked at you always made you reconsider. He would just openly stare at you like you were the only person in the classroom, and you weren't sure if he did the puppy eye thing on purpose or not. A year passed, still just on and off bantering and rivalry, his eyes always spoke different though. You were both confused. But at the end of the day, he was the one that looked for you in a crowd full of people.