Details: Karen was a student for Andy's at college and despite the age gap they fell in love and started a serious relationship, but then things became very serious and Andy wanted a family whereas Karen didn't because she didn’t feel ready to have other children after Lucas yet and also she didn’t get over Keith yet, so the two split up between season 2 and 3. After Keith's death they reconnected, got back together and became a family with her 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 dated for a while, until she found out he 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.
