Jim had seen Pam for the first time 7 times.

1. They were both 17. It was at a homecoming football game for her high school. She hadn’t seen him, but he saw her. He was sitting a couple rows in front of her. He saw when she was walking up the bleachers to meet her friends. To him she was beautiful in an understated way. Her hair was up, and she looked uncomfortable like she didn’t want to be at the game. Jim thought that if he could just meet her that they would hit it off and that they would start dating. He sat through the game and he saw her running down the steps, he was betting that she was trying to get out of there as fast as she could. He saw her run to a football player and wrap the football player in a kiss. Jim’s heart dropped. He didn’t think about that girl again until he was 23.
2. They were both 23. Jim walked into the office for his first day at work. He was greeted by a smile and kind eyes. Jim knew that this was the same girl from the football game all those years ago, he didn't say anything about that though. She spoke, "Hi. I'm Pam Beesly, you must be Jim." He nodded. This woman was stunning, and she seemed happy that there was someone else her own age working at the office now. He knew that she was right about not going back after meeting Dwight. At lunch he asked her if she wanted to go to Cugino's, she agreed. It was at lunch that she mentioned her fiance and Jim was crushed. Their lunch was fun, and they joked through the rest of the day. Jim at the end of the day saw her as his new best friend.
3. The third time they had been working together for about four years. In that time they had become close. They were best friends, even though Jim still wanted more. Their favourite things were playing pranks on Dwight and just laughing at their coworkers. This time when Jim saw Pam again for the first time was in November. They had just been laughing at Michael and his so called date with Jan, when he mentioned their night. He hadn’t meant to be so hurtful when he mentioned her worst first date. It was in the moment that she looked at him with total disgust, and loathing. That was like seeing her again for the first time, because she had never looked at him like that before. He again felt deflated. He knew that he shouldn’t have said that about Roy and Pam, but he was angry that she wasn’t willing to play along with his little joke about it being a romantic date.
4. The fourth time he couldn’t read her, but he knew he was seeing her again for the first time. She looked like a deer caught in headlights. He knew that was courtesy of him. He hadn’t meant to spring the news on her, but he had to do it sometime. It was right after the words had left his mouth, “I’m in love with you” that the look swept across her face. This time he hoped that this first look would be the one that would show her true feelings about him. It wasn’t. She just looked like she was about to be hit by a car, and he just left her. Her look after their first kiss was almost the same. The fourth first look was like they were strangers again, but with none of the warmth from their first meeting.
5. Their fifth first time was when Jim returned from Stamford. He saw her and she was just as beautiful at 28, as 23 if not more so. She had her hair done, and her face lit up when she saw him. This first time was awkward, but she was happy that he was back. He tried to make a joke, but she brushed it off. He didn’t know exactly where they stood, but he hoped that with this first look they would be friends again.
6. They were at the beach when the sixth first time happened. Pam had just done the coal walk; he had never seen her that invigorated in front of their coworkers. It was what she said, how she said it that made it seem like it was another first time. She was braver than he had ever seen her, and it was this time that he was left with the deer in headlights face. She had just admitted that she had called off her wedding for him. He was shocked with this new Pam, and he was surprised at how it was like seeing her as someone who he had never met again, a stronger more forceful Pam.
7. The seventh time was when he picked her up on their first official date. It was a look of pure joy. She was standing in front of him with this glow. Like she had been waiting for this for years. He knew that he had. This first look was the one that told him he would be able to have more than just friendship; this was the look that told him they would be together. He felt like he was on top of the world. The date was the single greatest experience he had ever had up to that point. He was so happy that she had said yes. He knew that after this first time he would be around to see even more first times.