Details: Karen was a student for Andy's at college and despite the age gap they started dating and started a serious relationship. But when Andy was deported Karen realized her feelings for Keith and ended their relationship as well as Andy wanted children whereas Karen didn't. After Keith's death the two reunited and together raised Karen and Keith's daughter Lily.
Details: They were highschool sweethearts and believed they would grow old together and he fathered her first child, Lucas Scott, but Dan then abandoned Karen and their son to go off to college. He then met Deb and had a child with her. In Season 4, they grew really close again after Keith's death and were on the way of reuniting, until she found out he was the one who had killed Keith.
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 her up from the airport. When she had finally forgiven him, he asked her to marry him, but said no. After the attempted murder of Dan, Karen finally realized that she loved Keith, they kissed and finally started a committed relationship. 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.
Details: After going on a Ravens away game together they realized they were able to get on well and they later went on to date although due to Karen's complicated relationship with Keith it never progressed to anything more.
