- „I have the hottest, smartest man on the planet. I don't need drama”
- —Naomi about Max[src]
Their romance started when they both attended West Beverly Hills High School. The two met when they were assigned as partners in a chemistry lab. Naomi was worrying about her money problems, due to Guru Sona, a con artist, stealing her money. Max unknowingly helped Naomi when he pointed out the land Guru Sona was building on was home to an endangered owl, allowing Naomi grounds to sue the Guru and get her money back. This event helped the two grow closer, and eventually agreed to be a couple as long as they kept it a secret (both were worried about their reputations; Max's as a nerd and Naomi's as a socialite). Finally they realized they could not have a successful relationship in secret, and came out to their friends.
Their relationship was seemingly perfect up until Max "edits" Naomi's final paper too much, causing her to be accused of cheating. Wanting to save Max's future, she tells the principle she did in fact cheat, giving up her place at CU and her graduation. While at the graduation, however, Max admits that he was the one who cheated while giving his valedictorian speech. After this, Max's parents are furious and forbid Max from seeing Naomi. The two are forced to briefly part ways until Naomi realizes she may be pregnant. Max accompanies her to the doctor, telling her that he will support her and the baby, and that they would have most likely ended up together anyway and are where they would have been in ten years: starting a family. He changes his tune however when the doctor reveals Naomi was not pregnant, acting overjoyed and hurting Naomi's feelings. The two break up.
Max returns when he gets a call from Holly, who wants to use him to ruin Naomi's chance of winning the Greek Games. When he shows up, the two reconcile, and start up where they left off. Things seem to be going well until Max realizes Naomi has feelings for a another CU student, Austin, and breaks up with Naomi. Ironically, after Naomi starts her business as an event planner, she is hired by Max's bride-to-be, Madison, to plan their wedding. Naomi is shocked when she finds out Max is her client's groom, and realizes she still has feelings for him. She tries to repress these feelings until the wedding day, when she runs down the isle to stop the wedding. Max realizes he can't marry Madison and the two elope after the wedding. They have high hopes for their marriage, but Max's best friend and business partner, Alec, does everything in his power to break up the couple. He first sets up Naomi, kissing her and having someone take photos of the kiss from afar. Alec shows the photos to Max, telling him Naomi hasn't changed her cheating ways and won't tell him about their kiss. When Naomi fails to tell Max about her and Alec's kiss, a Alec predicted she would, Max confronts her, leading to a fight.
Later, Naomi tries to prove that Alec is trying to sabotage their relationship by bringing Madison, Max's ex-fiance, back. She discovered that Alec had pressured Madison into hiring Naomi as their wedding planner, knowing that reintroducing the two old flames would ruin the wedding. Unfortunately, her plan backfires and Max ends up getting angry at both her and Alec, saying he is tired of having his best friend and wife fight. Naomi tells him he has to choose; her or Alec. Of course Max chooses Naomi, and Alec is forced to resign. Alec isn't done breaking up the couple, though. As Max searches for a new CEO for their company, Alec gets a candidate, Bryce, to infiltrate the company. He tells Bryce everything she needs to pass the interview and get hired as the new CEO, as long as she agrees to go to the board and have them agree to let Max go. When Naomi finds out about this, she confronts Alec. During this confrontation, she finds out the reason Alec sabotages Max's relationships is because he is actually in love with him himself. Naomi promises not to tell Max, because the truth would break his heart.
Max and Naomi's relationship begins to deteriorate after this. Naomi's controlling nature begins to get to Max, who runs away to his parents house to escape. They agree to get counseling once he returns. Suddenly, Max is offered a spot at MIT, where he believes he can start over from scratch and build a new company, since he and Alec began the old company in college. At hearing this, Naomi snaps, saying she is tired about hearing about "what Max wants." She has given up many opportunities for her career to be with him and support him, and believes he should do the same. They finally sit down and begin to talk about how maybe their marriage is hindering instead of helping them, causing them to lose their identities in each other. Later that night, Max leaves behind a goodbye note for Naomi.