| Description | ex. Girl and Boy |
| Brooke introduced them and they were a perfect couple until she got into drugs. | |
| She lost her virginity to him when he broke his soberity. | |
| They got divored and she moved in with her sister. | |
| They were married, but his wife passed away very young. | |
| He loved her all his life and helped take care of her son. They finally got together right before he died. | |
| They had a brief romance after chapperoning on an overnight weekend for the basketball team and the cheerleaders. | |
| He loves her and proposed to her so that she could stay in the United States, but she left. | |
| She sang at Tric and was Peyton's first client for her record label. She met him because he was the bartender at Tric. She broke up with him over text. | |
| They had one kiss, in hopes to make Brooke jealous when on a double date with Brooke and Owen. | |
| She broke her Clean Teens promise with this guy and ran out crying. She stopped talking to him completely. | |
| They shared a kiss at Quinn's gallery open and made a friend very angry. | |
| She tried everything she could to take this guy away from his wife. They shared one kiss but it meant nothing to him. She turned out to be crazy. | |
| She was feeling down and got him to agree to a date with her. | |
| She slept with him when she was really upset with Lucas. He serenaded her. | |
| He slept with her behind Victoria's back. | |
| She was a mean boss but he slept with her to get ahead at his job. | |
| She claimed to be having his baby, but in the end Dan proved that she was lying . | |
| They started liking each other almost instantly when she moved in with her sister and then fell in love. | |
| She began dating her sister's ex husband, right after the divorce. | |
| He was her high school teacher, but they slept together until she caught him in bed with the model from her show. | |
| He came on to Brooke's best friend at the time, in order to get her to keep her mouth shut about him and Brooke. | |
| She kissed her in her bedroom and it was a total shock for the other girl. | |
| He videotaped them having sex, so that people wouldn't believe he was gay. | |
| He was stalking her online and pretended to be her brother. They technically didn't hook up, but he tried to many times and almost killed her. | |
| They got married and had a TV show based on his book. She helped him get straight and he made her rich. They had a major age difference. | |
| She made out with this guy at a college party, only to find out that he was still in high school just like her. He was wearing Abercrombie and Fitch (hint for his name). | |
| They kissed a few times in high school but it meant way more to him than it did to her. She was a tease to him and never liked him as more than a friend. | |
| He has had a crush on her for all of high school. She went on a date with him and had a good time. They never actually shared a romantic kiss becasue they remained only friends. | |
| They dated when the show first began. They never had a stable relationship and they broke up shortly after the show began. He was awful to her. | |
| They went on one date after the Halloween dance at Tric. This never went anywhere because he wanted someone else. | |