- „I have the hottest smartest man on the planet. I don't need drama.”
- —Naomi about Max[src]
Max and Naomi met one day in high school as lab partners. At first, they didn't think much of each other. Max thought Naomi was an airhead; Naomi thought Max was a dork. But their chemistry was undeniable. One afternoon they found themselves on an impromptu field trip to confront Guru Sona, a con artist posing as a spiritual teacher, who tricked Naomi into “donating” away a large portion of her trust fund during a moment of weakness. Just when it seemed like there was no hope left for Naomi, Max revealed a loophole in the guru's scheme. They spent that night walking through the woods together, gathering evidence to help Naomi's cause. In that short time, they discovered common ground, and found that they worked well as a team. And Naomi, much to her dismay, realized she had "the hots for a nerd."
Naomi could not stop thinking about Max. She fantasized about him in her dreams, and at school. She tried to cover up her feelings, but found herself naturally opening up to him about her problems and taking his advice. He convinced her not to give up on her dream college, and helped save a charity project for her resumé. Overwhelmed by his generosity, Naomi gave in to her emotions and kissed him. She was shocked when Max rejected her, apologizing that she was "not (his) type."
Naomi did not take rejection lightly, and continued to pursue Max, first by trying to be like him, then by trying to seduce him. Max finally admitted that he was attracted to her, but felt she was too self absorbed. Naomi refused to give up, virtually humiliating herself in public for him. In the process, Max realized that she wasn't as arrogant as he thought. Naomi told him he was "funny, and smart, and freakishly confident"... and hot too. That was all Max needed; they kissed again, this time leaving them both breathless. To save their reputations, they agreed to keep the relationship a secret.
Max and Naomi continued to see each other privately, and their physical attraction went through the roof. One night in Max's bedroom, they finally had mind-blowing sex. Unable to stay away from him over spring break, Naomi concocted a cover story that Max was her math tutor and brought him to Cabo San Lucas, Mexico with her friends. The two spent most of vacation in their hotel room, studying calculus and each other. During this time, Max told Naomi that his feelings for her went way beyond sex. He really cared about her, and liked her for who she was.
Max and Naomi were still happy together... and still hiding it from everyone else. But as their relationship blossomed, it was getting harder for Naomi to contain her happiness, or her paranoia. Worried that Max was cheating on her, she followed him to an academic quiz bowl tournament, to spy on him and his teammate. When confronting them, she admitted her insecurities to Max. It made him realize how important she was to him, far beyond the stereotypes they were trying to protect. They officially came out as a couple, proudly walking through school arm in arm.
Max and Naomi's appeal was infectious; they were influencing similar pairings at school. The good news: They both got accepted to their first choice colleges. The bad news: The schools were on opposite coasts. Struggling with the idea of a long distance relationship, Naomi considered applying to Boston University to be near Max at MIT. Then Max announced to her that he already decided to attend CalTech and stay in LA to be near her. He believed that together they were strong enough to last.
Senior prom was fast approaching, and both Max and Naomi were looking forward to it. But beforehand, Naomi had to write an important paper to pass her history class. Max stayed up with her, successfully coaching her through it. Then at prom, they danced together all night, and Naomi was crowned Prom Queen. The evening ended on a sour note, however, when Naomi's history teacher accused her of cheating on her paper. Max confessed that he essentially rewrote the paper, afraid the original was not good enough for her to graduate.
Max and Naomi found themselves called to the principal's office on the last day of school. Hurt at first, Naomi tried to understand why Max cheated for her, guessing that he thought she wasn't smart enough. Max assured her that he thought she was "brilliant... hilarious, perceptive, and honest." Naomi forgave him, and ultimately, sacrificed her own college hopes for him, taking responsibility for the tainted paper. But Max had a moment of clarity during his valedictory speech. He revealed the truth about the paper in front of the entire graduating class, and was expelled. As further punishment, his parents forbade him from seeing Naomi, planning to ship him off to Cambridge for summer school and then college that fall. Max and Naomi said goodbye to each other in tears, and Max told Naomi he loved her. She told him she loved him too, but he was already gone. Later, after a freak accident, Naomi found herself in the ER getting a tetanus shot and blood tests. While there, she discovered she was pregnant, and went to Max the eve of his departure to tell him the news...
Max and Naomi were at the doctor's office. Both were still in shock about the pregnancy news. Max reassured Naomi that they could be good parents: they loved each other and wanted a life together; they just had to grow up a little faster than they anticipated. The doctor came in, and let them know that Naomi's first test was a false positive. They were in the clear: no baby. Both were relieved to hear the news, but Max overcompensated a bit, and said some hurtful things without thinking. As a result, Max and Naomi parted ways for the rest of the summer. In an effort to mend things, Max sent Naomi an apology letter, but she couldn't bring herself to read the whole thing, as it brought back up all her feelings for Max, and she was desperately trying to get over the loss of him. In a gesture of friendship, Annie saved Max's letter, knowing Naomi would want to know what it says someday.
During CU's Greek Games, Naomi's attention was deviously directed to a handsome bespectacled fan in the crowd, resulting in her getting slimed. It was Max! He came to talk to Naomi through Holly, who contacted him after stealing the letter he wrote from Annie's bedroom. Max also told Naomi that he decided to go to school at CalTech to be closer to her. He missed her, thought about her every day, and never stopped loving her. Naomi admitted that just seeing him made her feel like the best version of herself again. They reunited with a long, sweet kiss. Max celebrated Naomi's coronation as Head of the Greek Council with her sorority sisters. Austin tried to tempt Naomi away from Max, but she rejected him, proclaiming "That guy is the love of my life."
The local Congressional election was fast approaching. To entice an apathetic campus, Naomi decided to throw a big bash to educate students and register them to vote. Ever the supportive boyfriend, Max helped Naomi with the party preparations. Unaware of their history, Max mistakenly recruited Austin to help as well, and the cowboy again used the opportunity to push Naomi to cheat. Unable to handle the pressure, Naomi admitted to Max that she slept with Austin while they were broken up. But she also insisted that he brings out the best in her, and she would never risk losing that.
Max and Naomi were enjoying a leisurely game of gin rummy at her mansion. Max used it as an opportunity to show her some magic tricks. Delighted, Naomi transformed his talent into a winning act at a benefit to help Raj pay his medical bills. Despite their first prize, Max could not stand playing second fiddle to Naomi's unresolved feelings for another man. He painfully broke away from her, unable to accept anything less than her full commitment.
Months went by Naomi's relationship with Austin ended. She then met Preston, got engaged to him, and he broke her heart too. Doubtful that true love even existed, Naomi changed focus and threw herself into her new event planning business. She met a young heiress, Madison, who hired her to plan her wedding. The work suddenly became very personal when Madison introduced Naomi to her fiancé, Max. Seeing Max again made all of Naomi's feelings for him rise to the surface, and she finally admitted to her friends and to herself that she still and always has loved him. Naomi dug deep to unearth any of Madison's hidden flaws in an effort to stop the wedding and tell Max how she felt, but her plan sadly failed. When it seemed like all hope was lost and Naomi was about to let Max go, he confessed to her that he wasn't sure if he was doing the right thing by getting married so fast.
Naomi stepped in for Madison, Max's fiancée, when she became sick at their wedding rehearsal. Naomi walked down the aisle, kissed Max at the altar, and her "knees went weak". Overwhelmed, she ran out of the church, and Max followed her to make sure she was okay. Naomi reminded him there was no turning back after marriage, and asked him to explain why he confessed to her the night before his fear that he was making a mistake. Max told her he was so drunk from his bachelor party that he didn't even remember talking to her. Losing all hope and unable to endure the torture of seeing Max and Madison happy together for life, Naomi decided to take an immediate job offer from Rachel to manage her New York office. On her way out of town, she ran into Austin at the airport, and he enlightened her that Max was in fact completely sober at the bachelor party. Naomi realized their conversation outside the police station was an honest one, and rushed to stop the wedding. Just before Madison was about to put the ring on Max's finger, Naomi burst through the doors of the church and proclaimed her undying love to him. The entire church sat in stunned silence, and Naomi ran away humiliated. Later, Max found Naomi sitting on a hillside of the church grounds. He told her he could not go through with marrying Madison, because he was still in love with her. Taking Naomi's hand in his, Max confirmed their love was very mutual and very real.
The pair eloped at a Police Station shortly afterward, despite protestations from Max's friends and family that the marriage was a "huge mistake". One party particularly set against the marriage was Max's best friend Alec, who jumped at every possible opportunity to cause a rift in their love. He and Naomi fought on and off for months, confusing Max who didn't understand why they couldn't just get along. Finally, Naomi discovered that the reason Alec tried to break up all of Max's marriages was because he was gay and secretly in love with Max. Luckily, Alec did not want Max to know so this didn't cause him and Naomi any maritial troubles. However, Max and Naomi had begun fighting during this time because Naomi was trying to micro-manage Max's life. They went to see a marriage counsellor to no avail, so after a particularly heated argument they decided that they'd be better off apart, and filed for divorce. In the early days of their separation, Max and Naomi realized that despite all their arguments, they still had undeniable chemistry, and ended up hooking up a few times. However, Max dismissed those hook-ups as a "mistake" and went through with the divorce filings, much to Naomi's dismay. When she recieved the divorce papers, Naomi was very distraught and went out for a girls' night to try and drown her sorrows.