Details: When Lucas became part of the Ravens, he immediatly caught Brooke's eye and she started flirting with him, despite Lucas telling her that she didn't have to act that way around her. However, after Peyton was drugged and Brooke called Lucas, the two spent the night together caring for her and Lucas got to know Brooke, seeing a new side of her. They eventually formed a relationship after Lucas chose her over Peyton. But they later broke up after Lucas cheated on her with Peyton. Little over a year later they both feel in love with each other and despite issue they began a meaningful relationship although it ended after they grew apart.
Details: They fell for each other during the beginning of their junior year but since Lucas was dating Brooke they never started a proper relationship. A year later both moved on from their relationship with Brooke and Jake they once again started to date. But when they moved apart after high school they had little contact so when Lucas proposed to Peyton she told him later and they spilt. Three years later Peyton returned to Tree Hill were Lucas was engaged to Lindsey but they both had feelings for each other and after his failed wedding to Lindsey they began dating again and later got married and had a daughter, Sawyer.
Details: The two had a one night stand after meeting in a bar. But they soon discovered Nicki was Jake's ex-girlfriend and Jenny's mother and they tried to keep their fling a secret but a drunk Nicki revealed it later.
Details: After meeting on dare night the two began a relationship, although Anna's brother Felix and Lucas had a strained relationship due to Lucas dated Anna and Felix dating Lucas' ex Brooke Davis. The two had a good relationship but didn't sleep together as Lucas only wanted to sleep with someone had loved. Their relationship ended due to Anna's sexuality and Lucas' feelings for Brooke but they remained good friends.
Details: Upon arriving in Tree Hill Rachel flirted with Lucas but she never stated whether or not she was actually attracted to him. Their flirtatious friendship worked in both their favors for some time, as it allowed Lucas to make Brooke jealous (as Brooke was refusing to date him exclusively) and it also allowed Rachel to get under Brooke's skin and to find another way to anger her. Rachel knew, and appreciated, that Lucas was using her and allowed it but after the first basketball game of their senior year, Rachel told Lucas that she was done being part of his plan to make Brooke jealous and the two had very little contact from there on out.
Details: After starting to edit, Lucas Scott's first novel the two began to enter a romantic relationship and would split their time between; Tree Hill and New York. Lucas helped Lindsey through her father's death from cancer during their relationship. The first strains in their relationship began when Lucas' ex Peyton Sawyer returned to town and the couple would fight due to Peytons feelings for Lucas. Despite this the two became engaged and began planning their wedding. But on the wedding day Lindsey couldn't go through with it believing Lucas too had feelings for Peyton and left him at the alter. Lucas continually called and e-mailed Lindsey trying to recoiled their relationship, until he finally realized it was over.