Details: Brooke first met Julian when he came to Tree Hill in order to produce the movie version of Lucas Scott’s book "An Unkindness of Ravens" and the two started getting close. Julian was an ex-boyfriend Peyton Sawyer had for some time during the time jump between season 4 and 5 and while she was broken up with Lucas and at first it seemed that he came to Tree Hill to win her back. However, he ended up falling seriously in love with Brooke, who found herself in turn truly and maturely falling for someone for the first time after all her heartbreaks and the emotional instability she experienced during her life and also feeling really reciprocated like she never did. Their relationship had many bumps in the road with the biggest being Brooke’s inability to let her guard down and say “I love you” back to him because of all the reasons listed above. Feeling they were doomed, Julian went away, causing their relationship to end leaving both heartbroken, until Brooke decided to fly to LA to finally open up to him and tell him she loved him, so the two finally began an official committed relationship, splitting their time between LA and Tree Hill, until Julian, wanting to take their relationship to the next step, decided to move Tree Hill to settle down with Brooke, so they moved in together in her home. Julian then started working on a movie with the actress Alex Dupre, who set her sights on stealing him away from Brooke, while was told by doctors that she was unable to have children around this time, causing their relationship to falter once again. Fortunately, they quickly got back on track and Julian even proposed to Brooke while on vacation in Utah as she happily accepted. Despite Julian’s parents having problems with Brooke at first, they eventually accepted her and the two finally got married. Then, they attempted to adopt a child, but the birth mother changed her mind at the last minute, leaving the two devastated because it was basically their only chance to have a baby due to Brooke's apparent sterility, so they decided to move to New York for good, but suddenly Brooke found out that, by some miracle, she was pregnant after all, making them decide to definitely settle down in Tree Hill. She then gave birth to twin boys, whom she and Julian named Davis and Jude, and the newborn family finally had their happily ever after with all the Tree Hill gang.
Details: Brooke and Nathan had a one-night stand while Nathan was in a relationship with Peyton. The pair made a sex tape, which was played at a party during their senior year at Tree Hill High.
Details: When Lucas became part of the Ravens, he immediately caught Brooke's eye and she started aggressively flirting with him, despite Lucas telling her that she didn't have to act that way around him and showing hid evident disinterest in her. 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 better, seeing a deeper side of her. They eventually started dating after Peyton rejected him, but both realized immediately they had nothing in common and were very wrong for each other. Lucas soon broke up with Brooke anyway to be with Peyton because his feelings for her were too strong and he knew she was the one for him (even cheating on Brooke with her), causing a lot of strife between the three of them: in fact, Peyton tearfully decided to let Lucas go despite loving him out of guilt for betraying her best friend and then Brooke even pretended to be pregnant to take revenge on him. Despite this and the evidence of how unhealthy their relationship was, about one year later Lucas and Brooke got back together, but both soon had to face that nothing had changed: they still didn't have any real emotional connection and anything in common. So, after a brief romance, they eventually broke up for good, accepting once and for all they were not the right person for each other and not meant to be. Then, Lucas found his way back to Peyton, his one true love, while, in her young adulthood, Brooke finally met herself the love of her life, Julian Baker, whom she eventually got married to and had twin sons with.
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.
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: Nick and Brooke had some sort of a fling in the years between season 4 and season 5. He served as her date to Lucas and Peyton's wedding, and she used him to make Julian jealous.
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.
