Sophia Bush's Brooke Davis of One Tree Hill has become an iconic teen drama character that people still look up to even years after the show ended. Starting the show as a high school cheerleader and ending it as a business owner and mother of two, Brooke had a long journey over nine seasons of the show, where she matured into a happy, self-sufficient woman.
In addition to personal growth and career changes, Brooke went through a lot of challenges when it came to romantic relationships. Immediately, she was in the middle of the great Peyton and Lucas love triangle and searched long and hard for her true love. Along the way, she had some contenders, but only one person lived up to her expectations of what love should and could be.
Nick Chavez
During a time in which Brooke was making less than favorable decisions, she allowed Rachel to get her into the online dating scene, where she met and hooked up with Nick Chavez. The only catch was that he turned out to be her English teacher, and she was lying about her true age.
Even though what they were doing was incredibly wrong, they pursued the relationship in secret. Rachel eventually goes behind her friend's back in an attempt to end the relationship, which she knows is wrong and can only end badly. Later, Brooke finds out that Nick is cheating on her and Rachel comforts her. While the relationship with Nick was never solid, it allowed the bond between Rachel and Brooke to grow.
Nathan Scott
Brooke and Nathan's fling is only shown through flashbacks, depicting a time when Brooke and Peyton were at odds and a romantically involved Nathan and Peyton weren't getting along.
Not only did the two not have any chemistry, but the existence of their sexual tryst made their characters seem evil and cruel. Their betrayal of Peyton was uncalled for and a little unrealistic, especially for Brooke, who, despite her flaws, would never stoop as low as to sleep with her boyfriend.
Chris Keller
Similar to Brooke's involvement with Nathan, her relationship with musician Chris Keller was a one-time thing. After drunkenly bonding with him, the two slept together -- making for a decision Brooke later regretted.
During the time of their fling, Brooke and Chris Keller were both in difficult 'in-between' phases of their romantic relationships and were looking for comfort in the arms of another person. Unfortunately for Brooke, Chris wasn't the guy she wanted, Lucas was, and she left the situation unfilled and disappointed in herself.
Felix Taggaro
Following her first break-up with Lucas, Brooke fell for her annoying next-door neighbor, Felix Taggaro. They had an enemies-to-lovers story arc, even resulting to exclusively being friends with benefits for some time. However, they both developed feelings for one another and decided to attempt a real relationship.
Despite Felix's soft spot for Brooke, he was really mean to everyone else, even his own sister, Anna. Even though they grew to be fond of each other, Brooke couldn't stand for Felix's treatment of Peyton once he found out that Anna kissed her, and she promptly ended their relationship.
Nick Lachey
One Tree Hill had a lot of random celebrity cameos where they played themselves and pursued characters on the show (like Pete Wentz in season 3). Nick Lachey showed up in season 6 as a past romantic partner of Brooke during her time as a designer in New York.
In an attempt to make Julian, the man she is really after, jealous, she takes Nick as her date to Peyton and Lucas's wedding. Nick is a trooper for going along with Brooke's scheme but later tells her that he knows who she really wants to be with. The pairing isn't completely awful, but it does feel random and forced compared to Brooke's other love interests.
Owen Morello
Owen was Brooke's first real relationship following the time jump. The two formed a gorgeous couple in season 5, and he was seen to assist Brooke in helping Rachel get help as she struggled.
Owen and Brooke were a good match and a fun relationship for twenty-something Brooke Davis, however, she wanted to be a mom as soon as possible and he wasn't anywhere close to ready for that. They split up, but he eventually wanted her back despite her dreams of parenting. They were done for good after he slept with her friend, Millie, but the romance did serve as a good stepping stone relationship.
Chase Adams
Brooke and Chase developed a sweet relationship when he came to Tree Hill High School during their senior year. Chase was a member of the 'Clean Teens', a group of kids abstaining from sex. Brooke and Rachel later joined the group, where Brooke's crush on Chase developed and blossomed into a relationship.
Chase brought out a softer side of Brooke, as she wasn't able to use her usual sensual charm on him. Chase ended up losing his virginity to her at the end of senior year, and they broke up after they graduated. Brooke and Chase remained friends throughout the years, and she supported him in his other relationships and even attempted to set him up with Peyton at one point.
Lucas Scott
Since season 1, fans have been divided over whether or not to be Team Brucas (Brooke and Lucas) or Team Leyton (Lucas and Peyton). Despite the soulmate-like connection between Lucas and Peyton, Brooke's love for the older Scott brother gave their relationship a run for their money, and they could have worked out had he not broke her heart so many times.
Brooke and Lucas made a great couple, and allowed her to truly love someone other than herself as a teenager. He also made her realize that she deserved far better than him, as he was always going to be pining after her best friend. In some alternate reality where Peyton ends up with Jake, perhaps Brooke and Lucas also make it work.
Julian Baker
Julian Baker first made an appearance in season 6 as Peyton's ex-boyfriend in LA. He arrived in Tree Hill to make Lucas's novel into a movie and ended up falling head over heels for Brooke Davis.
Although initially skeptical and unable to let herself fully open up to him, Brooke eventually found herself in love with Julian. They had their problems (Alex Dupre, for one) but, at the end of the day, always ended up choosing each other. Julian was a perfect partner for Brooke because he was able to see all that she had to offer, and always chose her and their family first.