Details: When Lucas became part of the Ravens, he immediately caught Brooke's eye and she started provocatively flirting with him, despite Lucas telling her that she didn't have to act that way around him. However, after Peyton was drugged and Brooke called Lucas for help, the two spent the night caring for her and Lucas got to know Brooke, seeing a new side of her. They eventually started a relationship after Lucas chose her over Peyton. But they later broke up after Lucas cheated on her with Peyton. A little over a year later, they began a meaningful relationship. It later ended when Brooke and Lucas grew apart. Lucas then married Brooke’s best friend Peyton. Brooke, like many of the other characters on the show, realized early on that Lucas and Peyton were meant to be, stating that Lucas’s former fiancée Lindsey had no chance with Lucas: “I have been the Lindsey between Lucas and Peyton, and it’s not a great place to be.” Although Lucas, Peyton and Brooke had serious love triangle issues in their past, the three remained great friends.
Relationship: ex-Friends with Benefits / ex-Boyfriend
Details: Felix Taggaro moved in next door to Brooke during their junior year of high school. After many heated arguments and a lot of flirting, Brooke started a friends-with-benefits arrangement with Felix, not wanting to have a serious relationship where she could get hurt again. Soon, however, the two started to date and became a real couple. Brooke ended the relationship when she found out that Felix was the one who spray-painted “Dyke” on her best friend Peyton’s locker.
Relationship: Crush by Mouth, never reciprocated by Brooke / Best Friends
Details: Mouth developed a crush on Brooke in season 2 although she thought of him as a brother. But Mouth moved from his crush as Brooke didn't reciprocate his feelings. In the season 4 they went to prom together. In the finale of that season, he finally gathered the courage to kiss her. Subsequently, their friendship will grow more and more, during the various seasons, to be considered as one another as brother and sister.
Details: After being put together for the fantasy boy draft and with Haley begging Brooke she and Chris went on a date were after she saw her designs being used they drunkenly slept together, something Brooke regretted.
Details: After Rachel set Brooke up through on-line dating site as a twenty three year old she met Nick and that night they slept together. She later found out he was her new English teacher and they began a secret relationship until Rachel told of them. This resulted in Brooke finding out Nick had cheated on her and she ended the relationship.
Details: Brooke met Chase while she was a Clean Teen and they began dating. After Brooke revealed secrets they continued dating after a rough patch when Brooke promised there would be no more surprises. Later her sex tape with Nathan was revealed and they split up. They later reconciled due to their feeling for each other and Chase lost his virginity to Brooke. After high school they ended their relationship.
Details: The two dated started dating after Brooke flirted with him at Tric. When she took him to New York, he revealed that he was an addict after helping Rachel when she overdosed. The two ended their relationship when Brooke received temporary custody of Angie because he didn't want the commitment of a child.
Details: Brooke met Julian and the two became close when he came to Tree Hill in order to produce the movie version of Lucas Scott’s book "An Unkindness of Ravens". Julian was the ex-boyfriend of Peyton Sawyer, and at first it appeared that he had come to Tree Hill to win her back. However, he ended up falling for Brooke. Their relationship had many bumps in the road, the biggest being Brooke’s inability to let her guard down and say “I love you”. Julian went back to New York, causing their relationship to end until Brooke flew to New York to finally tell him she loved him. Julian and Brooke came back to Tree Hill and moved in together. Julian started work on a movie with actress Alex Dupre, who set her sights on stealing Julian away from Brooke. Brooke was also told by doctors that she was unable to have children around this time, causing their relationship to falter once again. They quickly got back on track, and Julian proposed to Brooke while on vacation in Utah. Despite Julian’s parents having problems with Brooke at first, the two got married. They attempted to adopt a child, but the birth mother changed her mind at the last minute, leaving the two devastated. The two decide to head back to New York for good, but Brooke finds out that by some miracle, she is pregnant after all. She gives birth to twin boys, and she and Julian name them Davis and Jude.