Total Sonic Island was where Maxie and Shawn first met. Unfortunatley, Shawn didn't leave a very good first impression. As a matter of fact, Maxie was completley disgusted by him. Shawn started to follow her around and persistantly ask her out or annoy her until she did. This went on so much that Sadie the Dog ended up stepping in and defending Maxie. Shawn just insulted her and left any time she appeared. Maxie complained about this constantly. Some viewers thought that Shawn and Maxie should end up together.
Because Shawn was voted off the show so early in the remake, he never had a chance to conflict with anybody, inculding Maxie. However, instead of conflict, he was very friendly to her when he came back in "Hide and Don't Speak" to help with the challenge. Though he found Maxie's hiding spot, he let her go to find another one, telling her she didn't deserve to be out so early. While she was leaving the kitchen, he told her to call him sometime, though he forgot to give her his phone number.
Because Shawn was in the first bunch of people to join the group, he and Maxie had a lot of time to interact. At first, he would flirt with her quite a bit, to which point she would just giggle and ignore it. After she dumped Ned, Shawn proceeded to flirt even more with her, and she even began to flirt back. Although being "warned" by Cliff to back off, he continued anyway with no bad repercussions. He eventually asked her out in the middle of season one, right before the new recruits arrived. Delighted, she happily accepted the request, and the two began to date for a while, devestating Cliff.
Near the beginning of season two, Maxie started trying to change Shawn, though he didn't mind at all until Razz told him it made him look like the woman in the relationship. After taking Razz's advice to be mysterious, Maxie got the idea that Shawn wasn't comfortable sharing things with her, and broke up with him because she said there was no trust.
From there onwards until season 3, Shawn and Maxie had little reaction, most likely avoiding each other. Maxie started taking charge of the A Team more and dropping Max off at the B Team, most likely because of the breakup. Shawn seemed hurt for about 2 episodes, then returned to he crazy pyromaniac jokester he was before.
During seasons three and four, Shawn would flirt with Maxie every now and again, though Sadie would tell him to back off many times. Maxie was the only person he would take orders from through the entire series, and he keeps a strong respect for her throughout.
During school, Maxie and Shawn's conflict was worse than ever. Then, their teacher assigned their class a project, and made Maxie and Shawn partners. Since they had to deal with eachother, Maxie thought it would make the most sense to explain some boundaries and whatnot. After school, the two went to Shawn's house. Here was their conversation:
- Shawn: So, you wanna make out?
- Maxie: Shawn, enough!
- Shawn: What's wrong, gorgeous?
- Maxie: I have a boyfriend! Stop flirting with me!
- Shawn: But I....
- Maxie: Fermez la bouche! I am tired of this! Why can't you be mature for 5 seconds? Stop doing this!
- Shawn: I... fine.
- Maxie: Fine what?
- Shawn: Fine. I'll stop flirting with you.
- Maxie: Really? Hmm. Good.
Maxie and Shawn started getting along better after getting an "A" on that project. They are not fairly close friends, but they are not enemies anymore. Sadie, however, still dislikes Shawn.