Details: Keith and Deb had always had a good relationship following her marriage to Keith's brother Dan Scott but following their break Keith was helping Deb clear out Dan's stuff and with the help of alcohol the two had a one night stand. But it wasn't followed by any other romantic feelings although they maintain a good ad close relationship.
Details: Keith and Emily or "Jules" as she was known meet while he was working at his brothers car dealership and started to date. They had a close relationship and Keith wanted her to have the same with his nephew who was like his son; Lucas Scott. But it turned out that Jules was hired but Keith's brother to seduce Keith and then dump him because Keith had slept with his wife. But it was only on the day of their wedding that Keith discovered this and they broke up for a while but once they reunited Keith realized he was still in love with Karen Roe.
Details: He was her friend for fifteen years. She kissed him before traveling to Florence, Italy. She then found out that Keith had been drinking when driving Lucas to pick Karen up from the airport. When she had finally forgiven him, he asked her to marry him. She said no. After the attempted murder of Dan, Karen finally realized that she loved Keith and they kissed. Keith was then arrested for his attempted murder. Later, Karen asked Keith to marry her with his response telling her that he was going to ask her. Soon after, Dan murdered Keith out of what he thought was getting revenge. Little known then, Keith died leaving Karen pregnant with her second child, a daughter, named Lily.